INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY
`ORGANIC CHEMISTRY DIVISION
`COMMISSION ON NOMENCLATURE OF ORGANIC CHEMISTRY
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`NOMENCLATURE OF
`ORGANIC CHEMISTRY
`
`Sections A, B, C, D, E, F and H
`
`1979 Edition
`
`Prepared for publication by
`J. RIGAUDY
`Universite Pierre et Marie Curie, Paris, France
`and
`S. P.KLESNEY
`The Dow Chemical Company, Midland, Michigan, USA
`
`PERGAMON PRESS
`
`OXFORD · NEW YORK · TORONTO · SYDN
`
`,·
`
`I
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`
`Illumina Ex. 1109
`IPR Petition - USP 10,435,742
`
`

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`U.K.
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`U.S.A.
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`CANADA
`
`AUSTRALIA
`
`FRANCE
`
`FEDERAL REPUBLIC
`OF GERMANY
`
`Pergamon Press Ltd., Headington Hill Hall,
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`
`Copyright© 1979 International Union of Pure and ,
`Applied Chemistry
`
`All Rights Reserved. No part of this publication may be
`reproduced, stored in a retrieval system or transmitted
`in any form or by any means: electronic, electrostatic,
`magnetic tape, mechanical, photocopying, recording or
`otherwise, without permission in writing from the
`copyright holders.
`
`SECTIONS A AND B
`First edition 1958, Second edition 1966
`Third edition 1971 (combined with Section C)
`Fourth edition 1979 (combined with Sections C, D, E, F & H)
`
`SECTION C
`First edition 1965
`Second edition 1971 (combined with Sections A & B)
`Third edition 1979 (combined with Sections A, B, D, E, F & H)
`
`SECTIONS D, E, F, H
`First edition 1979 (combined with Sections A, B &C)
`
`The contents of the first edition of Section C appeared in Pure
`and Applied Chemistry, Vol. 11, Nos. 1-2 (1965). The contents
`of the first edition of Section E appeared in Pure and Applied
`Chemistry, Vol. 45, No. 1 11976) and of the first edition of
`Section Hin Vol, 51, No, 2 (1979)
`
`British Library Cataloguing in Publication Data
`
`International Union of Pure and Applied Chemistry.
`Commission on the Nomenclature of Organic Chemistry
`Nomenclature of organic chemistry. - 4th ed.
`1. Chemistry, Organic - Nomenclature
`I. Title II. Rigaudy, J
`Ill. Klesney, SP
`547' .001 '4
`OD291
`79-40358
`ISBN 0-08-022369-9
`
`Printed in Great Britain by A. Wheaton & Co., Ltd., Exeter
`
`

`

`""''m"""'""""""~'"'i!llll•-------------
`
`t lE
`
`11 l I
`
`CONTENTS
`INTRODUCTION TO THE IUPAC REVISED AND
`COLLECTED RECOMMENDATIONS FOR THE
`NOMENCLATURE OF ORGANIC CHEMISTRY, 1978
`INTRODUCTION TO 1969 EDITION OF SECTIONS A,B & C
`PREFACE TO THE THIRD EDITION OF SECTIONS A AND B
`
`xv
`xvii
`3
`
`SECTION A
`
`Hydrocarbons
`
`ACYCLIC HYDROCARBONS
`A-1. Saturated unbranched-chain compounds and
`radicals
`A-2. Saturated branched-chain compounds and
`radicals
`A-3. Unsaturated compounds and univalent radicals
`A-4. Bivalent and multivalent radicals
`
`univalent
`
`univalent
`
`MONOCYCLIC HYDROCARBONS
`A-1 I. Unsubstituted compounds and radicals
`A-12. Substituted aromatic compounds
`A-13. Substituted aromatic radicals
`
`FUSED POLYCYCLIC HYDROCARBONS
`A-21. Trivial and semi-trivial names
`A-22. Numbering
`A-23. Hydrogenated compounds
`A-24. Radical names from trivial and semi-trivial names
`A-28. Radical names for fused cyclic systems with side chains
`
`BRIDGED HYDROCARBONS
`Extension of the von Baeyer system
`A--31. Bicyclic systems
`A-32. Polycyclic systems
`A-34. Hydrocarbon bridges
`
`SPIRO HYDROCARBONS
`A-41. Compounds: method l
`A-42. Compounds: method 2
`A-43. Radicals
`
`HYDROCARBON RING ASSEMBLIES
`A-51. Definition
`A-52. Two identical ring systems
`A-53. Non-identical ring systems
`A-54. Three or more identical ring systems
`A-55. Radicals for identical ring systems
`A-56. Radicals for non-benzenoid ring systems
`
`CYCLIC HYDROCARBONS WITH SIDE CHAINS
`A-61. General principles
`
`5
`
`5
`11
`14
`
`16
`18
`19
`
`20
`25
`27
`29
`31
`
`31
`31
`32
`35
`
`38
`40
`41
`
`42
`42
`43
`44
`45
`46
`
`46
`
`V
`
`

`

`~ -t ,_, .
`'
`
`CONTENTS
`
`TERPENE HYDROCARBONS
`A-71. Acyclic terpenes
`A-72. Cyclic terpenes
`A-73. Monocyclic terpenes
`A-74. Bicyclic terperies
`A-75. Terpene radicals
`
`SECTION B
`Fundamental Heterocyclic Systems
`SPECIALIST HETEROCYCLIC NOMENCLATURE
`B-1. Extension of the Hantzsch-Widman system
`B-2. Trivial and semi-trivial names
`B-3. Fused heterocyclic systems
`B-4. Replacement nomenclature ("a" nomenclature)
`B-5. Radicals
`B-6. Cationic hetero atoms
`HETEROCYCLIC SPIRO COMPOUNDS
`B-10. Compounds: method 1
`B-11. Compounds: method 2
`B-12. Radicals
`HETEROCYCLIC RING ASSEMB."LIES
`B--13.
`BRIDGED HETEROCYCLIC SYSTEMS
`B-14. Extension of the von Baeyer system
`B-15. Hetero bridges
`
`SECTION C
`Characteristic Groups Containing Carbon, Hydrogen, Oxygen, Nitrogen,
`Halogen, Sulfur, Selenium, and/or Tellurium
`PREFACE TO SECOND EDITION OF SECTION C
`PREAMBLE
`Scope of Section C
`Use of the rules
`Conventions
`Multiplying affixes
`Primed numbers or parentheses
`Numerals l (unity)
`Glossary
`Seniority; senior
`Elision of vowels
`Addition of vowels
`Terminal characteristic groups
`ortho-, meta-, para-
`
`Subsections
`C-0. NOMENCLATURE SYSTEMS
`0.0 General principles
`0.1 Substitutive nomenclature
`0.10 Characteristic groups
`Compulsory prefixes
`Principal group for citation as suffix
`
`48
`48
`49
`50
`50
`52
`
`53
`55
`64
`68
`70
`71
`
`72
`73
`73
`
`74
`
`75
`75
`
`79
`
`79
`79
`80
`80.
`81
`81
`81
`82
`82
`83
`83
`83
`
`85
`85
`85
`85
`87
`
`vi
`
`

`

`CONTENTS
`
`0.11 Exceptional treatment of some characteristic
`groups
`Carboxylic acids
`Derivatives and radicals from carboxylic acids
`Aldehydes and nitriles
`Amines
`0.12 Guide to construction of the name
`0.13 Seniority of chains (the principal chain)
`0.14 Seniority of ring systems
`0.15 Numbering of compounds
`0.16 Order of prefixes
`General procedure
`0.2 Radicofunctional nomenclature
`0.3 Additive nomenclature
`OA Subtractive nomenclature
`0.5 Conjunctive nomenclature
`0.6 Replacement nomenclature
`0. 7 Nomenclature of assemblies of identical units
`0. 8 Free radicals, ions, and radical ions
`Free radicals
`Cations
`Anions
`Two or more kinds of ionic centre with the same
`kind of charge in a single structure
`Positively and negatively charged ionic centres in a
`single structure
`PREAMBLE TO SUBSECTIONS C-1 to C-9
`C-1. HALOGEN DERIVATIVES
`C-2. ALCOHOLS, PHENOLS, AND THEIR DERIVATIVES
`Alcohols
`Phenols
`Heterocyclic compounds
`Radicals
`Salts
`Ethers
`Peroxides
`C-3. ALDEHYDES, KETONES, AND THEIR DERIVATIVES
`3.0 Aldehydes
`Acyclic aldehydes
`Cyclic aldehydes
`Trivial names
`3.1 Ketones
`General
`Carbocyclic and heterocyclic ketones
`3.2 Ketenes
`3.3 Acetals and acylals
`Acetals
`Acylals
`Acyloins (a-hydroxy ketones)
`C-4. CARBOXYLIC ACIDS AND THEIR DERIVATIVES
`4.0 Simple carboxylic acids
`.
`4.1 Hydroxy, alkoxy, and oxo acids
`
`89
`89
`90
`91
`91
`92
`97
`101
`105
`108
`108
`112
`114
`115
`118
`123
`127
`133
`133
`134
`139
`
`141
`
`142
`
`144
`
`148
`150
`153
`154
`155
`156
`16 l
`
`162
`162 ·
`163
`165
`167
`167
`1 71
`177
`178
`178
`181
`181
`
`182
`189
`
`vii
`
`{
`
`:}
`
`9
`9
`0
`,0
`:1
`: 1
`11
`l2
`l2
`33
`33
`33
`
`85
`85
`85
`85
`87
`
`

`

`CONTENTS
`
`4.2 Amino acids
`4.3 Amie acids
`4.4 Peroxy acids
`4.5
`Imidic, hydrazonic, and hydroxamic acids
`4.6 Salts and esters
`4. 7 Lactones, lactides, lactams, and lactims
`4.8 Acyl halides
`4. 9 Acid anhydrides
`
`C-5. COMPOUNDS CONTAINING BIVALENT SULFUR
`5.0
`Introduction
`5.1 Thiols and related compounds
`Thiols
`Hydropolysulfides
`Sulfides
`Polysulfides
`5.2 Sulfenic acids and their derivatives
`5.3 Thioaldehydes, thioketones, and thioacetals
`Thioaldehydes
`Thioketones
`Thioacetals
`5.4 Thiocarboxylic acids and thiocarbonic acid derivatives
`5.5 Sulfonium compounds
`
`C-6. SULFUR HALIDES, SULFOXIDES, SULFONES, AND
`SULFUR ACIDS AND THEIR DERIVATIVES
`6.1
`Introduction
`6.2 Organosulfur halides
`6.3 Sulfoxides and sulfones
`6.4 Sulfur acids and their derivatives containing sulfur
`directly linked to an organic radical
`6.5 Sulfur acids and their derivatives in which sulfur is
`linked only through oxygen to the organic radical
`6.6 Sulfur acids and their derivatives in which sulfur is
`linked only through nitrogen or through nitrogen and
`oxygen to the organic radical
`6. 7 Sultones and sultams
`
`G-7. COMPOUNDS CONTAINING SELENIUM OR
`TELLURIUM LINKED TO AN ORGANIC RADICAL
`'
`C-8. GROUPS CONTAINING ONE NITROGEN ATOM
`8.1 Amines
`General
`Primary amines
`Secondary and tertiary amines
`Ammonium compounds
`8.2 Amides and imides
`Monoacylamines
`DiR and triacylamines
`Imides
`
`193
`195
`196
`197
`199
`203
`206
`208
`
`210
`211
`211
`213
`213
`216
`217
`218
`218
`218
`220
`221
`227
`
`229
`229
`230
`
`233
`
`242
`
`243
`245
`
`247
`
`249
`249
`250
`254
`259
`261
`262
`266
`268
`
`viii
`
`

`

`CONTENTS
`
`8.3 Nitriles, isocyanides, and their derivatives
`8.4 Hydroxylamines and related compounds
`Hydroxylamines and their derivatives
`Oximes and their derivatives
`Amine oxides
`8.5 Nitroso and nitro compounds
`8.6 Amine radical ions
`
`THAN ONE
`
`C-9. GROUPS CONTAINING MORE
`NITROGEN ATOM
`9.1 Azo and azoxy compounds
`Azo compounds
`Azoxy compounds
`9.2 Hydrazines and their derivatives
`9.3 Diazonium and related groups
`9.4 Groups containing three or more contiguous nitrogen
`atoms
`9.5 Compounds containing a N=C-N or N=C=N group
`Ami dines
`Amide oximes
`Amidrazones
`H ydrazidincs
`Pormazans
`Carbodiimides
`9.6 Compounds containings a N-C=N group
`
`J
`
`9. 7 Compounds containing a N-00-N or related group
`9.8 Compounds containing a N-CO-N-N or more com~
`plex group
`
`LIST OF RADICAL NAMES
`
`269
`272
`272
`273
`274
`275
`275
`
`277
`277
`283
`284
`289
`
`291
`292
`292
`294
`294
`295
`295
`295
`296
`
`297
`
`301
`305
`
`SECTION D
`Organic Compounds Containing Elements that are not Exclusively Carbon,
`Hydrogen, Oxygen, Nitrogen, Halogen, Sulfur, Selenium and Tellurium
`
`D-0. PREAMBLE
`0.1 Scope of Section D
`0.2 Conventions
`0.3 Terminology
`
`D-1. NOMENCLATURE SYSTEMS
`1.1
`Inorganic nomenclature of binary compounds
`1.2 Coordination nomenclature
`1.3 Substitutive nomenclature
`1.31 Choice of the functional class of a
`characteristic group
`1.32/3 Choice between characteristic groups
`bound to the same structure
`1. 34/ 6 Choice of a parent between two
`directly bound characteristic groups
`
`323
`324
`324
`
`326
`327
`327
`
`328
`
`328
`
`331
`
`ix
`
`ti
`
`;.·•.\: ..
`
`9
`9
`0
`4
`9
`,1
`i2
`i6
`i8
`
`

`

`CONTENTS
`
`1.4 Radicofunctional nomenclature
`1.5 Additive nomenclature
`1.6 Replacement nomenclature
`1.7 F_undamental heterocyclic systems
`
`D-2. COORDINATION COMPOUNDS
`2.0
`Introduction
`2.1 Definitions
`2.2 Principles of coordination nomenclature
`2.21 Formulae
`2.22 Names
`Indication of oxidation number and
`2.23
`proportion of constituents
`2.24 Terminations
`2.25 Structural prefixes
`2.3 Ligands
`2.31/4 Anionic ligands
`2.35/7 Neutral and cationic ligand
`2.38 Different modes of linkage of some
`ligands
`2.39 Designation of active coordination
`sites among several possibilities
`2.4 Abbreviations
`2.41 General principles
`2.42 Anionic groups
`2.43 Neutral groups
`2.5 Coordination entities with unsaturated
`molecules or groups
`2.51 Designation of stoicheiometric
`composition only
`2.52/ 4 Designation of structure
`2.55/9 Dicyclopentadienyl coordination
`compounds of metals: metallocenes
`2.6 Designation of isomers
`2.61/3 Geometrical isomerism
`2.64 Chiral isomerism
`2.7 Dinuclear and polynuclear compounds with
`bridging groups
`2.71/3 Compounds with bridging atoms
`or groups
`2.74 Extended structures
`2.8 Dinuclear and polynuclear compounds without
`bridging groups
`2.81/2 Direct linking between centres of
`coordination
`2.83 Homoatomic aggregates
`
`D-3. ORGANOMETALLIC COMPOUNDS
`3.0
`Introduction
`3.1 Organometallic compounds in which the metal
`is bound to organic radicals and hydrogen only
`3.2 Organometallic compounds having uncharged
`ligands
`
`X
`
`331
`332
`334
`336
`
`337
`337
`338
`338
`338
`
`339
`339
`339
`340
`340
`342
`
`344
`
`345
`345
`345
`346
`346
`
`347
`
`348
`348
`
`349
`351
`353
`355
`
`355
`
`355
`357
`
`358
`
`358
`359
`
`360
`
`361
`
`363
`
`'/
`
`

`

`CONTENTS
`
`3.3 Organometallic compounds having anionic
`ligands
`3 .4 Organometallic radicals
`3. 5 Organic radicals containing characteristic
`groups
`3 .6 Organometallic compounds with two or more
`metal atoms
`3. 7 Organometallic ions
`
`D-4. CHAINS AND RINGS WITH REGULAR PATTERNS
`HETERO ATOMS
`4.0
`Introduction
`4.1 Homogeneous chains
`4.2 Homogeneous rings
`4.3 Chains of alternating atoms limited by
`identical atoms
`4.4 Chains of repeating units
`4.5 Rings of repeating units
`4.6 Radicals from chains and rings of repeating
`units
`4.7 Substituents
`
`364
`366
`
`367
`
`369
`370
`
`OF
`
`373
`373
`375
`
`376
`377
`378
`
`380
`380
`
`382
`
`384
`
`389
`392
`
`393
`
`395
`
`399
`
`406
`408
`
`409
`409
`411
`414
`
`415
`
`417
`
`D-5. ORGANIC COMPOUNDS CONTAINING PHOSPHORUS,
`ARSENIC, ANTIMONY OR BISMUTH
`5.0
`Introduction
`5 .1 Phosphines, their analogues and their metal
`derivatives (Coordination number 3)
`5 .2 Phosphines and their analogues containing
`electronegative substituents (halogen, OH,
`SH, SeH, NH?, etc) and their derivatives
`(Coordination71umber 3)
`5.3 Onium compounds (Coordination number 4)
`5.4 Phosphine oxides and their analogues
`(Coordination number 4)
`5.5 Oxo acids containing quinquevalent phosphorus
`and arsenic (Coordination number 4)
`5 .6 Derivatives of oxo acids containing
`quinquevalent phosphorus and arsenic
`(Coordination number 4)
`5.7 Phosphoranes and their analogues
`(Coordination number 5)
`5.8 Anions (Coordination number 6)
`
`D-6 ORGANOSILICON COMPOUNDS
`6.0
`Introduction
`6.1 Chains and rings of silicon atoms
`6.2 Chains and rings of silicon and oxygen atoms
`6.3 Chains and rings of silicon and sulfur atoms
`6.4 Chains and rings of silicon and nitrogen
`atoms
`6.5 Radicals and compounds having more than one
`chain
`
`xi
`
`I
`
`··L ,[
`
`l
`l \_
`
`·'.
`'
`
`'!' ,.__, __
`
`l
`
`3
`
`

`

`CONTENTS
`
`6.6 Silasesquioxanes, silasesquithianes, etc
`6.7 General nomenclature systems
`6.71 Replacement nomenclature
`6.72 Extended Hantzsch-Widman nomenclature
`6. 73/ 5 Coordination nomenclature
`6.76/8 Compounds having a silicon-metal bond
`6. 79 Compound radicals
`6.8 Substituting groups
`6. 9 Esters
`
`D-7. ORGANOBORON COMPOUNDS
`7 .0
`Introduction
`7 .1 Boron hydrides
`7 .2 Polyboranes with skeletal replacement
`7 .3 Boron radicals
`7.4 Derivatives of the boron hydrides
`7.5 Heterocyclic boron compounds
`7 .6 Organoboron coordination compounds
`7. 7 Organoboron addition compounds
`
`APPENDIX
`
`Table I - Seniority list of elements and "a"
`terms used in replacement nomenclature,
`in decreasing order of priority
`Table II - Element radical names
`Table HI - Affixes used in inorganic
`nomenclature
`Table IV - Trivial names for heterocyclic
`systems
`
`SECTION E
`Stereochemistry
`
`INTRODUCTION
`E.1. Types of isomerism
`E.2. cis-trans-Isomerism
`E.3. Fused rings
`E.4. Chirality
`E.5. Conformations
`E.6. Stereoformulae
`
`Appendix I. Configuration and conformation
`Appendix IL Outline of the sequence rule
`procedure
`
`SECTION F
`General Principles for the Naming of
`Natural Products and Related Compounds
`
`PREAMBLE
`
`xii
`
`418
`419
`419
`420
`420
`422
`423
`423
`426
`
`429
`429
`432
`433
`434
`440
`447
`454
`
`459
`461
`
`464
`
`466
`
`473
`473
`475
`478
`479
`483
`484
`
`486
`
`486
`
`491
`
`

`

`CONTENTS
`
`;,f;:
`·:_-_
`(:;
`/·
`
`F .1. Biologically based trivial names
`F.2. Parent structures for semisystematic names
`F.3. Degree of saturation or unsaturation
`F.4. Modification of the parent structure
`F.5. Substituents
`F.6. Stereochemistry
`
`SECTION H
`
`lsotopically Modified compounds
`
`INTRODUCTION
`
`H-1. SYMBOLS, DEFINITIONS, AND FORMULAE
`1.1 Symbols
`1.11 Nuclide symbols
`1.12 Atomic symbols
`1.2 Definitions and formulae of various types
`of isotopic modification
`1.21 Isotopically unmodified compounds
`1.22 Isotopically modified compounds
`1.23 Isotopically substituted compounds
`1.24 Isotopically labeled compounds
`1.25 Specifically labeled compounds
`1.26 Selectively labeled compounds (unknown
`mixture)
`1.27 Selectively labeled compounds (known
`mixture)
`1.28 Nonselectively labeled compounds
`1.29 Isotopically deficient compounds
`
`493
`494
`496
`497
`508
`508
`
`513
`
`513
`513
`513
`
`514
`514
`514
`514
`514
`514
`
`515
`
`517
`517
`518
`
`H-2. NAMES FOR ISOTOPICALL Y MODIFIED
`2.1
`Isotopically substituted compounds
`2.2 Specifically labeled compounds
`2.3 Selectively labeled compounds
`2.4 Nonselectively labeled compounds
`2.5
`Isotopically deficient compounds
`2.6 General and uniform labeling
`2. 7 Exceptional changes in the names of some
`unsymmetrically modified compounds
`2.8 Order of nuclide symbols
`2. 9 Stereo isomeric isotopically modified
`compounds
`
`COMPOUNDS
`518
`519
`522
`524
`524
`524
`
`H-3. NUMBERING OF ISOTOPICALLY MODIFIED
`COMPOUNDS
`3.1 Numbering in relation to the unmodified
`compound
`3.2 Priority between isotopically modified
`and unmodified atoms or groups
`
`I ,
`
`xiii
`
`525
`526
`
`527
`
`530
`
`531
`
`

`

`CONTENTS
`
`H-4. LOCANTS FOR NUCLIDES IN ISOTOPICALLY
`MODIFIED COMPOUNDS
`4.1 Omission or introduction of locants
`4.2 Location of nuclides on positions of
`compounds that are normally not
`assigned locants
`
`REFERENCES
`
`APPENDIX Comparative examples of formulae and
`names for isotopically modified compounds
`
`INDEX
`
`533
`
`534
`
`537
`
`538
`
`539
`
`xiv
`
`

`

`INTRODUCTION TO THE IUPAC REVISED
`AND COLLECTED RECOMMENDATIONS FOR
`THE NOMENCLATURE OF ORGANIC
`CHEMISTRY, 1978
`
`The progress of the IUPAC Connnission on the Nomenclature of Organic
`Chemistry during the period 1969 to 1977 has been reported in the Comptes
`Rendus of the Conferences (Reconnnended Rules) or in the Information Bulletin
`of the Union, Appendices on Provisional Nomenclature, Symbols, Units and
`Standards (Provisional Rules). While work for improving and completing
`nomenclature rules continues, we have now reached the point where it is possi(cid:173)
`b.le and convenient to collect in a single volume a compendium of existing
`reconnnendations providing improved guidance to internationally agreed nomen(cid:173)
`clature.
`
`The Sections included in this compendium are
`
`Section A. Hydrocarbons
`
`Section B. Fundamental Heterocyclic Systems
`
`Section C. Characteristic Groups containing Carbon, Hydrogen, Oxygen,
`Nitrogen, Halogen, Sulfur, Selenium and/or Tellurium
`
`These Rules are the IUPAC Organic Nomenclature Rules Sections A,
`Band C, 1969, reprinted from the combined edition, Butterworths,
`London (1971), corrected for material errors.
`
`Section D. Organic Compounds containing elements that are not exclusive(cid:173)
`ly Carbon, Hydrogen, Oxygen, Nitrogen, Halogen, Sulfur,
`Selenium and Tellurium.
`
`These Rules are issued jointly by the Organic and Inorganic Nomen(cid:173)
`clature Connnissions, and were published originally in IUPAC Infor(cid:173)
`mation Bulletin, Appendix No.31, August 1973. Corrections for mate(cid:173)
`rial errors and a few revisions have been introduced into the pro(cid:173)
`visional text after evaluation of connnents.
`
`xv
`
`

`

`Section E. Stereochemistry
`
`INTRODUCTION
`
`These Rules are IUPAC Recommendations 1974 and are reprinted from
`Pure and Applied Chemistry, Vol. 45, pp. 11-30 (Pergamon, 1976)
`with a few corrections for material errors.
`
`Section F, General Principles for the Naming of Natural Products and
`
`Related Compounds
`
`These Rules have not been finally approved, but their inclusion
`
`here seems appropriate (some minor errors have been corrected),
`
`Section H. Isotopically Modified Compounds
`
`These Rules, now approved, were originally published in the IUPAC
`
`Information Bulletin, Appendix No. 62, July 1977. Corrections for
`r:1a terial errors have been introduced after evaluation of comments.
`
`Although the titles of these Sections are .to a large extent self-exp la(cid:173)
`
`natory, it is thought useful here to make some comments on the arrangement
`of material. Glossaries of terms used are to be found in the Introduction to
`the 1969 Rules, p. xviii and in Section C, p. 81.
`
`The attention of a reader having a nomenclature problem to solve is
`drawn first to Section C, which deals initially with general principles for
`
`the construction of a name. The operations described in this Section are
`usually to be applied to the names for hydrocarbons and heterocyclic systems
`provided by application of the Rules in Sections A and B.
`
`Section D contains various types of material (see contents pp. ix-xii),
`
`some of which would be more appropriately included in earlier sections ; for
`
`example, much of Rules D-1 (Nomenclature Systems, p. 326 ), D-4 (Chains and
`Rings with Regular Patterns of Heteroatoms, p. 373), D-6 and D-7 (Organosili(cid:173)
`
`con and Organoboron Compounds, pp. 409-458), and the Appendix Tables I, II and
`IV (pp.459-47I)falls into this category. We hope to reorganise the subject
`
`matter in a later edition.
`
`i
`;I
`.f
`i\,
`1.,
`
`jl
`
`1!
`'I
`If;
`H
`
`i',
`'i
`
`xvi
`
`

`

`INTRODUCTION TO 1969 EDITION OF SECTIONS
`A, B AND C
`
`The first international proposals on the nomenclature oforganic chemistry,
`made at Geneva in 1892, were revised and extended by the Definitive
`Report of the Commission for the Reform of Nomenclature in Organic
`Chemistry of the International Union of Chemistry (I.U.C.) which appeared
`after the meeting at Liege in 1930 (Liege Rules), and was supplemented by
`less extensive reports from the meetings at Lucerne in 1936 and at Rome
`in 1938. Although these proposals rendered great service, it was apparent
`at the meeting of the International Union of Pure and Applied Chemistry
`(I.U.P.A.C.) at London 'in 1947 that extension and revision of the
`nomenclature rules for organic chemistry were required.
`Those who have served on the Commission on the Nomenclature of
`Organic Chemistry for varying periods from 194 7 to 1969 are M. Betti*,
`R. S. Cahn, L. T. Capell, L. C. Cross, G. Dupont*, G. M. Dyson, C. S.
`Gibson*, H. Grunewald, G. Kersaint, S. P. Klesney, K. L. Loening,
`N. Lozac'h, R. Marquis*, A. D. Mitchell*, H. S. Nutting, A. M. Patterson*,
`V. Prelog, F. Richter*, J. Rigaudy, S. Veibel, P. E. Verkade, and E. _
`Votocek*, and, as observers, K. A. Jensen
`(chairman, I.U.P.A.'C.
`Commission on the Nomenclature of Inorganic Chemistry), W. Klyne
`(member of the IUPAC/IUB Commission for Biochemical Nomenclature).
`The Commission's progress in the period 1947 to 1969, inclusive, has
`been reported in successive issues of the Comptes Rend us of the Conferences
`of the Union. Relevant parts of those reports are included, with a few
`revisions, in the rules which form the body of this publication.
`Comments on these rules should be sent to the Secretary, S. P. Klesney,
`3609 Boston, Midland, Michigan 48640, U.S.A. or to any other member of
`the Commission.
`
`GENERAL PRINCIPLES
`The Commission believes that differences in nomenclature frequently
`hinder the accurate and intelligible conveyance of information from one
`chemist to another, so tending to hamper understanding and progress.
`The .Commission urges conformity with internationally agreed nomenclature
`even when this nomenclature may not seem the best possible from the
`point of view of the chemists of a particular nation or group.
`The rules now presented are intended to be suitable for text books, journals
`and patents, for lexicons and similar compilations, and for indexes, even if
`not always wholly so for conversation or lectures. The rules will be issued
`in parts, as they become approved by the Union. They constitute recom(cid:173)
`mendations for the naming of types of compounds and of individual
`compounds. They are not exhaustive, except in specified cases. Where,
`for various reasons, limitation to a single method of nomenclature appears
`undesirable or impossible, alternatives are given; but the C~mmission
`hopes that elimination of alternatives may become acceptable as the merits
`of one method become more generally recognized. The Commission hopes
`also that each nation will try to reduce the variations in nomenclature with
`regard to spelling, the position of numbers, punctuation, italicizing,
`abbreviations, elision of vowels, certain terminations, and so forth;
`the
`* Deceased.
`
`xvii
`
`~--
`
`

`

`present rules are not to be held as making recommendations in these matters.
`
`INTRODUCTION
`
`Owing to the very extensive nomenclature which has come into being
`since the last revision, the Commission has, in the main, confined its efforts
`to codifying sound practices which already existed, rather than to originating
`new nomenclature-the latter may form a later stage of the Commission's
`activities.
`In so doing, the Commission had in mind the following main principles:
`(a) as few changes as possible should be made in existing nomenclature,
`though utility is more important than priority; (b) rules and names should
`be unequivocal and unique, but simple and concise; (c) records in journals,
`abstracts, compendia, and industry should be used to assess the relative
`extent of past use of various alternatives; (d) rules should be consistent with
`one another, yet aid expression in the particular field of chemistry involved
`and be capable of extension with the progress of science; (e) trivial names,
`and names having only a very small systematic component, cannot be
`eliminated when in very common use, but those of less value should be
`replaced by systematic (or at least more systematic) ones, and the creation
`of new trivial names should be discouraged by provision of extensible
`(f) naIT3;es should be adaptable to different
`systematic nomenclature;
`languages. The Commission is aware that acceptance of its recommenda(cid:173)
`tions depends in,large measure on the success which has attended its attempts
`to assess, for each particular case, the relative merits of these often conflicting
`claims.
`
`GLOSSARY
`
`The Commission considered it unnecessary to define chemical terms in
`common use. However, certain terms which have special meaning in
`nomenclature merit brief description; namely:
`
`Parent compound: the principal chain or ring system from which a name is
`derived by substitution of hydrogen with other atoms or groups; e.g.
`methylcyclohexane has cyclohexane as its parent.
`Systematic name: a name composed wholly of specially coined or selected
`syllables, with or without numerical prefixes; e.g., pentane, oxazole.
`Trivial name: a name no part of which is used in a systematic sense;
`e.g., xanthophyll.
`Semi-systematic name or semi-trivial name: a name of which only a part is
`used in a systematic sense; e.g., methane (-ane), butene (-ene), calciferol
`( -ol).
`(Most names in organic chemistry belong to this class.)
`Substitutive name: a name involving replacement of hydrogen by a group
`or by another element; e.g., 1-methylnaphthalene, 1-pentanol.
`Replacement name: an " a" name, where C, CH, or CH 2 is replaced by
`a hetero atom; e.g., 2, 7,9-triazaphenanthrene. Also, certain names
`
`xviii
`
`

`

`i j
`
`INTRODUCTION
`
`involving thio- (also seleno- or telluro-) to indicate replacement of oxygen
`by sulfur ( or selenium or tellurium, respectively); e.g., thiopyran.
`Subtractive name: a name involving removal of specified atoms; e.g., in
`the aliphatic series names ending in -ene or -yne. Also names involving
`anhydro-, dehydro-, deoxy-, etc., or nor-.
`Radicefunctional name: a name formed from the name of a radical and the
`name of a functional class; e.g., acetyl chloride, ethyl alcohol.
`Additive name: a name signifying addition between molecules and/or
`atoms; e.g., styrene oxide.
`Conjunctive name: a name formed by placing together the names of two
`molecules, it being understood that the two molecules are linked by los~ of
`one hydrogen atom from each; e.g., naphthaleneacetic acid.
`Fusion name: a name 'for a cyclic system formed by use of a linking " o "
`between the names of two ring systems, denoting that the two systems are
`fused by two or more common atoms; e.g., benzofuran.
`Hant,zsch-Widman name: a name for a heterocyclic system, derived from the
`original proposals of Hantzsch and Widman, and formetl from a prefix or
`prefixes (to denote one or more hetero atoms) and a suffix -ole or -ine (to
`denote a five- or a six-membered ring, respectively); e.g., triazole, thiazole.
`
`Bibliography
`
`1928, pp. 63-71
`
`International Union of Pure and Applied Chemistry
`Comptes rendus of the 9th Conference
`International Union of Chemistry
`Comptes rendus of the 10th Conference
`Comptes rendus of the 12th Conference
`Comptes rend us of the 13th Conference
`Comptes rendus of the 14th Conference
`International Union of Pure and Applied Chemistry
`Comptes rendus of the 15th Conference
`1949, pp. 127-186
`·
`1951, pp. I 00-104
`Comptes rend us of the 16th Conference
`Comptes rendus of the 18th Conference
`1955, pp. 120-184
`Patterson, A. M., Capell, L. T., and Walker, D. F. The Ring Index, 2nd ed.,
`American Chemical Society, Washington, D.C., 1960
`Hantzsch, A., and Weber, J. H., Ber. Dtsch. Chem. Ges. 20, 3119 (1887)
`Widman, 0., J. Prakt. Chem., [2], 38, 185 (1888)
`Baeyer, A., Ber. Dtsch. Chem. Ges. 33, 3771 (1900)
`
`1930, pp. 57-64
`1936, pp. 39-42
`1938,pp. 36-37
`1947, pp. 129-137
`
`xix
`
`

`

`1
`1
`
`r
`
`UNSATURATED COMPOUNDS
`
`A-3.1
`
`(d) The chain having the least branched side chains.
`
`CH 2-CH 2-CH 3
`sl
`1
`2-4
`6
`7-11
`12
`CH 3-(CH 2) 3-CH-CH-(CH 2) 5-CH 3
`I
`CH 3-(CH 2) 3-CH-CH-CH 3
`I
`CHa
`
`6-( 1-Isopropylpentyl)-5-propyldodecane
`
`Rule A-3. Unsaturated Compounds and Univalent Radicals
`
`3.1-Unsaturated unbranched acyclic hydrocarbons having one double
`bond are named by replacing the ending " -ane " of the name of the
`corresponding saturated hydrocarbon with the ending "-ene ". If there
`are two or more double bonds, the ending will be " -adiene ", " -atriene ",
`etc. The generic names of these hydrocarbons (branched or unbranched)
`are "alkene", "alkadiene", "alkatriene", etc. The chain is so numbered**
`as to give the lowest possible numbers to the double bonds. When, in cyclic
`compounds or their substitution products, the locants of a double bond
`differ by unity, only the lower locant is cited in the name; when they differ
`by more than unity, one locant is placed in parentheses after the other (see
`Rules A-31.3 and A-31.4).
`
`Examples:
`
`6
`5
`4
`3
`2
`1
`CH 3-CH 2-CH 2-CH=CH-CH 3
`
`1,4-Hcxadiene
`
`l
`2
`3
`4
`5
`6
`CH 3--CH =CH-CH 2-CH =CH 2
`
`The following non-systematic names are retained:
`
`Ethylene
`
`Allene
`
`CH 2=0=0H 2
`
`* Here the choice lies between two possible main chains of equal length, each containing
`six side chains in the same positions. Listing in increasing order, the number of carbon
`atoms in the several side chains of the first choice as shown and of the alternate second
`choice results as follows:
`
`first choice
`second choice
`
`I, I, 1, 2, 8, 8
`1, 1, I, I, 8, 9
`
`The expression, " the greatest number of carbon atoms in the smaller side chains", is taken
`to mean the largest side chain at the first point of difference when the size of the side chains
`is examined step by step, Thus, the selection in this case is made at the fourth step where
`2 is greater than 1.
`**Only the lower locant for a double bond is cited in the name of an acyclic compound .
`
`11
`
`

`

`A-3.2
`
`ACYCLIC HYDROCARBONS
`
`3.2-Unsaturated unbranched acyclic hydrocarbons having one triple
`bond are named by replacing the ending " -ane " of the name of the
`corresponding saturated hydrocarbon with the ending " -yne ".. If there
`are two or more triple bonds, the ending will be "-adiyne '', "-atriyne ",
`etc. The generic names of these hydrocarbons (branched or unbranched)
`are" alkyne "," alkadiyne ", "alkatriyne ", etc. The chain is so numbered
`as to give the lowest possible numbers to the triple bonds. Oni;r the lower
`locant for a triple bond is cited in the name of a compound.
`The name "acetylene" for HC==CH is retained.
`3.3-Unsaturated unbranched acyclic hydrocarbons having both double
`and triple bonds are named by replacing the ending " -ane " of the name
`of the corresponding saturated hydrocarbon with the ending "-enyne ",
`"-adienyne ", "-atrienyne ", "-enediyne ", etc. Numbers as low as
`possible are given to double and triple bonds even though this may at
`times give " -yne ,, a lower number than " -ene "., When there is a choice
`in numbering, the double bonds are given the lowest numbers.
`Examples:
`
`1,3-Hexadien-5-yne
`
`3-Penten-1-yne
`
`1
`2
`3
`4
`5
`6
`HC==C-CH=CH-CH=CH 2
`