NAMING ORGANIC COMPOUNDS A Systematic Instruction Manual 2nd edition

Transcription

1 NAMING ORGANIC COMPOUNDS A Systematic Instruction Manual 2nd edition E. W. GODLY, B.Sc.C.Chem.MRSC Formerly Head of the Nomenclature Subdivision of Laboratory of the Government Chemist Teddington, Middlesex ELLIS HORWOOD for and COMMISSION OF THE EUROPEAN COMMUNITIES

2 Author's note 1 Introduction 1.1 Aimsandfunctions 1.2 How to use the book 1.3 Selection principles 1.4 Editorial practices and Conventions 1.5 Definitions of terms used in the flow-diagram notes 2 Stereochemistry 2.1 Optical isomerism 2.2 Geometrical isomerism 3 Silicon chains 3.1 Silicon-only chains Straight chains Branched chains 3.2 Silicon/oxygen chains of alternating atoms Straight chains Branched chains 3.3 Silicon/sulphur chains of alternating atoms 3.4 Silicon/carbon chains 4 Heterochains 5 Hydrocarbon chains 5.1 Unbranched chains Saturated Unsaturated

3 VI 5.2 Branchedchains 5.3 Substituted derivatives 6 Monocycloalkanes 7 Monocycloaikenes 7.1 Unsubstituted 7.2 Substituted derivatives 8 Single-ring aromatics 8.1 Unsubstituted 8.2 Substituted derivatives 9 Heteromonocycles [Box 9 reached by the route (v)-(viii)-(ix)] 9.1 Trivials 9.2 Other saturated small rings containing N 9.3 Other single-ring heterocycles of three to ten atoms 9.4 Partially hydrogenated forms 9.5 Rings ofmorethan ten atoms 9.6 Substituted derivatives 9.7 Box 9 reached by the route (viii)-(xiv)-(xx)-(xxiii)-( 10 Monocy clic hy drocarbons with attached chain(s) 11 Bicyclic spiro-hydrocarbons 11.1 Saturated 11.2 Unsaturated 11.3 Substituted derivatives 12 Two-ringaromatichydrocarbons 12.0 Introduction 12.1 Fused rings 12.2 Biphenyl derivatives 12.3 Assembliesof two-ringaromatichydrocarbons 13 Two-ring 'alks' 13.1 Two rings of equal size in close association Rings joinedby a Single bond Saturated ormancunide Partially hydrogenated forms 13.2 Two dissimilar rings directly linked 13.3 Identical or dissimilar rings with two shared atoms Saturated Unsaturated

4 Substituted derivatives Rings not in close association Heterospiro Compounds Benzo/hetero two-ring Systems Mancunide structures Trivially named Adaptation of Hantzsch-Widman System to benzo-heteromonocycles Hydrogenated forms Fused heterocycles having two rings Trivially named forms Fusion Numberingthe fused System Bonding and indicated hydrogen Hydrogenated forms Substituted derivatives Multi-ring heterocycles Assembliesof threeor more identical monocycles Substituted derivatives of monocycleassemblies Systems with threeor more rings fused together Assembliesof fused heterocyclic Systems Substituted derivatives (sections ) Multi-ring carbocycles Trivially named ring-systems Fused polycyclic hydrocarbons Othermodesof close association All identical structures The structure containing two or more identical units directly linked Assembliesof fused polycarbocycles The structure having no direct linkage between identical units Bridged Systems Bicyclo Compounds Fused ring aromatic and heterocyclic base-components Cages More complex polycyclic spiro-compounds Spiro-linkage between identical polycyclic components Spiro-linkage between different polycyclic components Substituted and hydrogenated derivatives 92 vn

5 Vlll YELLOW PAGES Seniority of ring-systems, chains and ring-with-chain Systems A. Ring-systems B. Chains C. Seniority of ring-system vs. chain 21 Radicofunctionais General notes Cations Acylhalides Ring-flankedketonesandthioketones Unsubstituted monoketones Substituted derivatives Polyketones,non-collectable Hydrazones Oximes Unsubstituted oximes Substituted derivatives of oximes Stereoisomers Polyoximes Radico-alcohols Esters of inorganicacids Hydroperoxides Amines Triviallynamedphenylmonoamines Othermonoamihes Primary Secondary Tertiary Diamines Triviallynamedphenyl diamines Othercoilectable diamines Collectable diamines not symmetrically N-substituted Guanidines Polyamines with threeor more nitrogen atoms All primary with twoor more collectable One or more secondary or tertiary Individual chains with four or more non-terminal, non-contiguous nitrogen atoms Non-collectable polyamines (including diamines) Imines 119

6 21.11 Ethers General Trivially named ethers Mono-ethers, systematic radicofunctional names Di-and poly-ethers Sulphidesandpolysulphides Monosulphides Polysulphides Sulphoxides Sulphones Peroxides Azides Oxides Vario-functional acyclic Compounds Subsidiary flow-diagram Carboxylic acids with trivial names covering more than one kind of subsidiary f unctional group Trivial names covering COOH and afunctional group COOH plus either -COOM or -COOR: acid salts and acid esters COOH plus-c( = 0)-N<: amic acids COOH plus -CHO: aldehydicacids COOH plus >C=: keto acids (oxo acids) COOH plus-oh: hydroxy acids COOH plus-n<:amino acids Aminosulphonic acids Derivatives of the trivially named acids of sections Salts and esters Acylhalides Nitriles Carboxylic amides Aldehydes Substituted derivatives Vari-functional cyclic Compounds Introduction The PG and one or more FGscoveredbya trivial name Carboxylic acids Amic acids Aldehydic acids Hydroxy acids Amino acids Etheric acids Amino-sulphonic acids 146 ix

7 Aldehydes Acyloins Functional derivatives of acids of sections and Anions Saltsandesters Acylhalides Amides Amidines Nitriles Aldehydes Substituted derivatives Mono-PG ring-systems Preamble Carboxylic acids Trivially named Systematically named Peroxy acids Cyclicanhydrides Thioic and dithioic acids Sulphonic acids Anions Salts Esters Lactones and lactams Lactones Lactams Acidhalides Urea derivatives Amides Carboxamides Sulphonamides Carbothioic amides Hydrazides Imides Amidines Nitriles Aldehydes Ketones The >C=0 group attached directly to two separate ring-systems The >C=0 group attached also toachain The >C=0 group occupyinga ring position Thioketones 167

8 24.20 Oximes Alcohols and their metal derivatives Triviallynamed alcohols Systematically named alcohols Metal derivatives of alcohols Phenols and their metal derivatives Trivially named phenols Systematically named phenols Hydrogenatedforms Metal derivatives of phenols Esters of inorganic acids (other than HX) Thiols Substituted derivatives Mono-PGchains Carboxylic acids Triviallynamed Systematically named Peroxy acids Monothioic acids Dithioic acids Sulphonic acids Salts Carboxylic anhydrides Esters Esters of carboxylic acids Esters ofcarbothioic acids Esters of sulphonic acids Esters of inorganic acids Lactones Acylhalides Carbothioic halides Halides of sulphonic acids Ureas Amides Amidines Nitriles Aldehydes Ketones Thioketones Alcohols, their metal derivatives and esters with mineral acids Alcohols Metal derivatives ofchain alcohols Esters ofchain alcohols with mineral acids Thiols 195 XI

9 Xll 26 Poly-PGacyclics Preamble Polybasiccarboxylic acids Trivially named saturated dicarboxylic acids Trivially named unsaturated dicarboxylic acids Other dicarboxylic acids Acids withthreeormore COOHgroups Carboxylic acid derivatives Sulphonic acids and their derivatives Other acids Ketones Polyols Assembliesof identical units Basic unsubstituted structures Substituted derivatives Poly-PG cyciic Systems Preamble Carboxylic acids Trivially named Systematically named Thioic acids Functional derivatives of acids Non-cyclyzing Cyclyzing Anhydrides Cyciic esters Imides Polyketones >C=Oadjacenttoaring-system >C=Oadjacenttotworing-systems >C=Ooccupyingaringposition Quinones Non-quinonoidring-polyketones Cyciic polyols Trivially named Systematically named Assemblies Structures containing two nitrogen atoms directly linked Preamble Hydrazines Azo-compoundsR'-N = N-R Diazo and diazonium Compounds Chainsofthreeormore nitrogen atoms 224

10 Appendix A. Classes of Compound not covered in the book Xlll 226 Appendix B. Rules for special-structure Compounds B-l Cephalosporins B-2 Ergoline derivatives B-3 Morphines B-4 Penicillins B-5 Tetracyclines Appendix C. Radicals (attached groups) C-0.1 Nomenclatureof radicals C-0.2 Recognition of radicals C-0.3 Citationof radicals in aname C-1 Radicals derived from carbon chains C-l.l Univalent C-l.1.0 Preamble C Saturatedunbranched C-l.l.2 Saturated branched C-l.l.3 Unsaturated C-1.2 Divalent C-1.3 Multivalent C-2 Heteroatomic and composite radicals C-2.1 Monovalent heteroatomic radicals C-2.2 Composite monovalent radicals C-2.3 Acyl radicals C-2.4 Ionicforms C Cations formed by gaining a proton C Anions formed by loss of a proton from an acid C-2.5 Divalent chain radicals C-3 Cyclic radicals C-3.1 Monovalent C General C Hydrogenated forms C Ring-with-chain radicals C-3.2 Divalent C-4 Substituted radicals C-4.1 Open chain radicals C-4.2 Substituted cyclic radicals C-4.3 Composite radicals C Name-construction principles C Substituted composite divalent radicals for use in assembly names

11 xiv Appendix D. Guide to name-construction 255 D-l Formation ofnames 255 D-l.l Substitutive nomenclature 255 D-l.2 Radicofunctional nomenclature 257 D-2 Numbering 258 D-2.1 Molecularstructures 258 D-2.2 Radicals 260 D-3 Name-construction usingworkedexamples 261 Table 1 Functional groups usable as name-endings 265 Table 2 Groups which cannot have suffix-status always cited as prefixes 270 Table 3 Heterocyclic prefixes for replacement nomenclature (in decreasing order of priority) 270 Flow-diagram