Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters

Authors

  • C. Hootelé Service de Chimie Organique - Faculté des Sciences - Université Libre de Bruxelles, Belgique
  • J.P. Lenders Service de Chimie Organique - Faculté des Sciences - Université Libre de Bruxelles, Belgique

DOI:

https://doi.org/10.2533/chimia.1974.665

Abstract

Nicotine reacts with chloroformic esters to give the chloro-carbamates resulting from the cleavage of the C2' –N1' bond. The reaction is shown to proceed with at least 96 to 98 % inversion of configuration. In the same way, (R)-(+)-N,N-dimethyl-α-phenethylamine gave (S)-(−)-α-phenethyl chloride with inversion.

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Published

1974-11-30

Issue

Vol. 28 No. 11 (1974): Forschung/Research

Section

Kurze Mitteilungen

License

Copyright (c) 1974 C. Hootelé

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
C. Hootelé, J. Lenders, Chimia 1974, 28, 665, DOI: 10.2533/chimia.1974.665.