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Ring-transformation reactions of 5-hydroxy-2-oxabicyclo[3.2.0]-heptan-4-ones and 5-hydroxy-2-oxabicyclo[3.2.0]hept-6-en-4-ones

✍ Scribed by Tetsuro Shimo; Hidemi Minamishin; Kenichi Somekawa

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
196 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Dehydrochlorination of chlorinated 5‐hydroxy‐2‐oxabicyclo[3.2.0]heptan‐4‐ones, 3a‐c, which were obtained from the photo[2+2]cycloadditions between 4‐hydroxy‐3(2__H__)‐furanone 1 and chloroethylenes, with triethylamine gave 2‐ethenyl‐3(2__H__)‐furanones 4a,b or 2‐(2‐cyanoethyl)‐3(2__H__)‐furanone 4c. 2‐Oxa‐bicyclo[3.2.0]hept‐6‐en‐4‐ones 7 being [2+2]cycloadducts between 1 and acetylenes gave 2,3‐dihydro‐3‐oxooxepin derivatives 8 by electrocyclic rearrangement.

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