Helvetica Chimica Acta

The carbon zip reaction: a method for expanding carbocycles

Y Nakashita, M Hesse

Index: Nakashita, Yoshihiko; Hesse, Manfred Helvetica Chimica Acta, 1983 , vol. 66, # 3 p. 845 - 860

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Citation Number: 47

Abstract

Abstract A general method for enlargement of carbocyclic rings by the so called zip reaction is given. The Michael adducts of 2-nitrocycloalkanones with 3-oxo-4-pentenoates in the presence of tetrabutylammonium fluoride give in high yield compounds with the ring enlarged by four C-atoms. By this method 7-, 8-, and 12-membered cycloalkanones were converted respectively to 11-, 12-, and 16-membered functionalized carbocycles (see ...