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

Research output: Contribution to journalArticleResearchpeer-review

9 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

Cite this

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title = "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",
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.",
author = "{George Burrowes}, T. and {Roy Jackson}, W. and Suellen Faulks and Irene Sharp",
year = "1977",
month = "1",
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pages = "1855--1858",
journal = "Australian Journal of Chemistry",
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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. / George Burrowes, T.; Roy Jackson, W.; Faulks, Suellen; Sharp, Irene.

In: Australian Journal of Chemistry, Vol. 30, No. 8, 01.01.1977, p. 1855-1858.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - 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

AU - George Burrowes, T.

AU - Roy Jackson, W.

AU - Faulks, Suellen

AU - Sharp, Irene

PY - 1977/1/1

Y1 - 1977/1/1

N2 - 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.

AB - 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.

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U2 - 10.1071/CH9771855

DO - 10.1071/CH9771855

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JF - Australian Journal of Chemistry

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