CSIRO Publishing

An international journal for chemical science

Shopping Cart: ( empty )

RESEARCH ARTICLE

Previous Next Contents Vol 60(8)

Stereochemical Study of 2-Substituted N-Vinylpyrroles

Leonid B. Krivdin ^A ^B , Yury Yu. Rusakov ^A , Elena Yu. Schmidt ^A , Al'bina I. Mikhaleva ^A and Boris A. Trofimov ^A

+ Author Affiliations

- Author Affiliations

^A A. E. Favorsky Institute of Chemistry, Irkutsk, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia.

^B Corresponding author. Email: krivdin_office@irioch.irk.ru

Australian Journal of Chemistry 60(8) 583-589 https://doi.org/10.1071/CH07086
Submitted: 25 March 2007 Accepted: 24 May 2007 Published: 9 August 2007

Abstract

Stereochemical study of five 2-substituted N-vinylpyrroles obtained via the Trofimov reaction was carried out based on the experimental measurements of their ¹³C–¹H and ¹³C–¹³C spin–spin coupling constants substantiated by the high-level ab initio calculations of the parent 2-methyl-N-vinylpyrrole. The title compounds were shown to adopt a predominantly skewed s-trans conformer with a noticeable population (approximately 10%) of the higher-energy skewed s-cis conformation, however, with the exception of 2-tert-butyl-N-vinylpyrrole adopting almost entirely a skewed s-trans conformation.

Acknowledgments

Financial support from the Russian Foundation for Basic Research (Grant no. 05–03–32231) is gratefully acknowledged.

References

[1] Katritzky A. R. , Rees C. W. , Scriven E. F. V. , Comprehensive Heterocyclic Chemistry 1996 (Pergamon Press: Oxford).

[2] Trofimov B. A. , The Chemistry of Heterocyclic Compounds, in Pyrroles (Ed. R. A. Jones) 1992, p. 131 (Wiley Interscience: New York, NY).

[3] Schmidt E. Yu. , Mikhaleva A. I. , Vasiltsov A. M. , Zaitsev A. B. , Zorina N. V. , Arkivoc 2005, 7, VM-1231J, 11.

[4] Mikhaleva A. I. , Schmidt E. Yu. , Selected Methods for Synthesis and Modification of Heterocycles (Ed. V. G. Kartsev) 2002, p. 331 (IBS Press: Moscow).

[5] (a) M. V. Sigalov, B. A. Trofimov, Russ. J. Org. Chem. 1995, 31, 801.


        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |

        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |

        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |

        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar | [Verified 7 June 2007].

[15] (a) T. H. Dunning, J. Chem. Phys. 1989, 90, 1007.
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |

        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |