Extension and Revision of the von Baeyer System for Naming Polycyclic Compounds (Including Bicyclic Compounds)
(IUPAC Recommendations 1999)

VB-9

Continued from VB-8.3 to VB-8.5

Contents of Section

VB-9 Configuration of Chiral Systems
References


VB-9 Configuration of Chiral Systems

The configuration of a chiral ring system with a unique numbering determined by the structure is specified by the R/S system. It may thus be necessary to specify whether the name refers to one enantiomer, a racemate, or is only indicating relative configuration.

Example


(1S,2R,4R,5S)-3,6,8-trioxatricyclo[3.2.1.02,4]octane
CAS index name = [1S-(1[alpha],2[alpha],4[alpha],5[alpha])]-3,6,8-trioxatricyclo[3.2.1.02,4]octane

Note A different method of indicating stereochemistry has been adopted by CAS starting with volume 129 of Chemical Abstracts. This would also apply to the names given in VB-8.5.

If it is required to specify that this name applies to a racemate, or that only the relative stereochemistry is known the prefixes rac- or rel- may be used. Thus for the example above:
This example(1S,2R,4R,5S)-3,6,8-trioxatricyclo[3.2.1.02,4]octane
Its enantiomer(1R,2S,4S,5R)-3,6,8-trioxatricyclo[3.2.1.02,4]octane
Racemic sample(1RS,2SR,4SR,5RS)-3,6,8-trioxatricyclo[3.2.1.02,4]octane
orrac-(1R,2S,4S,5R)-3,6,8-trioxatricyclo[3.2.1.02,4]octane
Relative configuration only(1R*,2S*,4S*,5R*)-3,6,8-trioxatricyclo[3.2.1.02,4]octane
orrel-(1R,2S,4S,5R)-3,6,8-trioxatricyclo[3.2.1.2,4]octane

References

1. A. Baeyer, Systematik und Nomenclatur bicyclischer Kohlenwasserstoffe, Ber. Dtsch. Chem. Ges., 33, 3771-3775 (1900). (Although he always published his research as just Baeyer he was always referred to with the honorific as von Baeyer.)

2. E. Buchner and W. Weigand, Bornylen und Diazoessigester [Nebst einer Nomenklatur tricyclischer Kohlenstoff-Ringsysteme nach Adolf von Baeyer], Ber. Dtsch. Chem. Ges., 46, 2108-2117 (1913).

3. A.M. Patterson, Proposed international rules for numbering organic ring systems, J. Am. Chem. Soc., 47, 543-561 (1925); A.M. Patterson, The nomenclature of parent ring systems, J. Am. Chem. Soc., 50, 3074-3087 (1928).

4. A.M. Patterson and L.T. Capell, The Ring Index, Reinhold, New York, 1940; A.M. Patterson, L.T. Capell and D.F. Walker, The Ring Index, 2nd edition, American Chemical Society, Washington, DC, 1960 (Supplements 1963, 1964 and 1965). This was continued as the Parent Compound Handbook and then the Ring Systems Handbook 1993 ed., Chemical Abstracts Service, Columbus, Ohio, 1993 (and November 1997 cumulative supplement).

5. Chemical Abstracts Service, Index Guide, Appendix IV, 1997.

6. International Union of Pure and Applied Chemistry, Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F and H, 1979 edition, Pergamon Press, Oxford, 1979.

7. International Union of Pure and Applied Chemistry, A Guide to IUPAC Nomenclature of Organic Compounds, Recommendations 1993, Blackwell Scientific Publications, Oxford, 1993.

8. IUPAC Commission on the Nomenclature of Organic Chemistry, Treatment of variable valence in organic nomenclature (Lambda convention) (Recommendations 1983), Pure Appl. Chem., 56, 769-778 (1984).

9. IUPAC Commission on the Nomenclature of Organic Chemistry, Revised nomenclature for radicals, ions, radical ions and related species (IUPAC recommendations 1993), Pure Appl. Chem., 65, 1357-1455 (1993).

10. D.R. Eckroth, A method for manual generation of correct von Baeyer names of polycyclic hydrocarbons, J. Org. Chem., 32, 3362-3365 (1967).

11. G. Rücker and C. Rücker, Nomenclature of organic polycycles out of the computer - how to escape the jungle of the secondary bridges, Chimia, 44, 116-120 (1990).

12. IUPAC Commission on the Nomenclature of Organic Chemistry, Nomenclature of fused and bridged fused ring systems (IUPAC recommendations 1998), Pure Appl. Chem., 70, 143-216 (1998).

13. IUPAC Commission on the Nomenclature of Organic Chemistry, Revision of the extended Hantzsch-Widman system of nomenclature for heteromonocycles (Recommendations 1982), Pure Appl. Chem., 55, 409-416 (1983).

14. IUPAC-IUB Joint Commission on Biochemical Nomenclature, Nomenclature of Steroids (Recommendations 1989), Eur. J. Biochem., 186, 429-458 (1989); Pure Appl. Chem., 61, 1783-1822 (1989) and in Dictionary of Steroids (eds R.A. Hill, D.N. Kirk, H.L.J. Makin and G.M. Murphy) Chapman and Hall, London, 1991, pp xxx-lix; IUBMB, Biochemical Nomenclature and Related Documents, second edition, Portland Press, London, 1992, pp 192-221.

15. L.A. Paquette, M.A. Kesselmayer, G.E. Underiner, S.D. House, R.D. Rogers, K. Meerholz and J. Heinze, Multifaceted consequences of holding two [8]annulene rings face-to-face. Synthesis, structural characteristics, and reduction behaviour of [22](1,5)cyclooctatetraenophane, J. Am. Chem. Soc., 114, 2644-2652 (1992).


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