Reaction of 5-Chloroalkyl-3-phenyl-4,5-dihydroisoxazoles with strong base. An unexpected new synthesis of the 2-Oxa-3-azabicyclo[3,1,0]hex-3-ene ring system

T. George Burrowes, W. Roy Jackson, Suellen Faulks, Irene Sharp

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11 Citations (Scopus)

Abstract

Reaction of 5-chloromethyl-3-phenyl-4,5-dihydroisoxazole with potassium t-butoxide in dimethyl sulphoxide gives 4-phenyl-2-oxa-3-azabicyclo[3,1,0]hex-3-ene in high yield and reaction of the 5-(1'-chloroethyl) homologue gives high yields of the diastereoisomeric 6-methyl derivatives of the bicyclic system. Some unsuccessful attempts to convert these bicyclic compounds into substituted cyclo-propanols and cyclopropenes are described.

Original languageEnglish
Pages (from-to)1855-1858
Number of pages4
JournalAustralian Journal of Chemistry
Volume30
Issue number8
DOIs
Publication statusPublished - 1 Jan 1977

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