Studien zur Biidung von Cyclopropan- und Oxiran-Derivaten in der Dreikomponentenreaktion von Basen, α-Halogen-acrylsäure-derivaten und Carbonylverbindungen

Authors

  • R. Scheffold Institut für Organische Chemie der Universität Bern Erlachstraße 9 a, CH-3000 Bern 9
  • P. Bissig Institut für Organische Chemie der Universität Bern Erlachstraße 9 a, CH-3000 Bern 9
  • K.L. Ghatak Institut für Organische Chemie der Universität Bern Erlachstraße 9 a, CH-3000 Bern 9
  • B. Granwehr Institut für Organische Chemie der Universität Bern Erlachstraße 9 a, CH-3000 Bern 9
  • B. Patwardhan Institut für Organische Chemie der Universität Bern Erlachstraße 9 a, CH-3000 Bern 9

DOI:

https://doi.org/10.2533/chimia.1975.463

Abstract

The competitive formation of oxiranes 1 and cyclopropanes 2 in the reaction of 2-halogeno-acrylic acid-derivatives, carbonyl-compounds and bases is discussed. The product ratio 1: 2 depends strongly upon the acidity of the carbonyl-compound as well as the structure of the acrylic acid-derivative. Cyclopropanes 2 are predominantly formed in the base-induced reaction of 2-halogeno-acrylic acid-derivates and CH-acids bearing two geminal acidic H. Oxiranes 1 on the other hand are produced in a three-component-condensation of 2-halogeno-acrylic acid-derivatives, carbonyl-compounds and carbanions of CH-acids of a pKa 8 to 15, bearing only one acidic H. The utility of glycidonitriles 1b as intermediates is demonstrated by the conversion of 1b into the γ-keto-δ-spirolactone 4.

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Published

1975-11-30

Issue

Vol. 29 No. 11 (1975): Forschung/Research

Section

Kurze Mitteilungen

License

Copyright (c) 1975 R. Scheffold

Creative Commons License

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

How to Cite

[1]
R. Scheffold, P. Bissig, K. Ghatak, B. Granwehr, B. Patwardhan, Chimia 1975, 29, 463, DOI: 10.2533/chimia.1975.463.