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Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam

Agathocleous, D., Cox, Graham and Page, Michael I. (1986) Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam. Tetrahedron Letters, 27 (14). pp. 1631-1634. ISSN 0040-4039
Abstract

The cycloaddition of succinimido ketene to 2,3-dihydrofuran yields P- -succinimido bicyclo [3.2.0] 2-oxoheptan-6-one. This unusual stereochemistry is confirmed by 1H NMR and X-ray crystallography. The cyclobutanone product undergoes ring opening in concentrated hydrochloric acid to give 1-succinimido-5-chloro-2-pentanone.

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Article
Depositing User:
Sharon Beastall
Date Deposited:
11 Nov 2009 13:30
Revision:
11
Last Modified:
28 Aug 2021 10:52
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