1,3-dipolar cycloadditions of 2-Ethoxy- and 2-(ethylthio)-1-azetines with nitrile oxides, nitrile ylides and nitrilimines: An unexpected 1,2,4-triazole formation.

Karl Hemming, Abdul Bassett N. Luheshi, Alan D. Redhouse, Robert K. Smalley, J. Robin Thompson, Peter D. Kennewell, R. Westwood

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

2-Ethoxy- and 2-(ethylthio)-1-azetines readily undergo 1,3-dipolar cycloadditions with nitrile oxides and nitrile ylides to give stable 4,5-bicyclic cycloadducts. With nitrilimines, however, the expected 1,3-dipolar cycloadducts and/or unexpected ring-opened products, namely 1,2,4-triazoles, are formed depending on the nature of the nitrilimine N-substituent. In contrast, the azetines fail to react with nitrile sulphides, azomethine ylides, nitrones, aryl azides, and various dienes. X-ray crystallographic data on the nitrile oxide, nitrile ylide, and nitrilimine cycloadducts, and on the 1,2,4-triazoles, are presented. Also a mechanistic rationale for triazole formation is offered.

LanguageEnglish
Pages4383-4408
Number of pages26
JournalTetrahedron
Volume49
Issue number20
DOIs
Publication statusPublished - 1 Jan 1993
Externally publishedYes

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Azetines
Nitriles
Cycloaddition
Cycloaddition Reaction
Oxides
Triazoles
Azides
Sulfides
X-Rays
1,2,4-triazole
X rays

Cite this

Hemming, Karl ; Luheshi, Abdul Bassett N. ; Redhouse, Alan D. ; Smalley, Robert K. ; Thompson, J. Robin ; Kennewell, Peter D. ; Westwood, R. / 1,3-dipolar cycloadditions of 2-Ethoxy- and 2-(ethylthio)-1-azetines with nitrile oxides, nitrile ylides and nitrilimines : An unexpected 1,2,4-triazole formation. In: Tetrahedron. 1993 ; Vol. 49, No. 20. pp. 4383-4408.
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1,3-dipolar cycloadditions of 2-Ethoxy- and 2-(ethylthio)-1-azetines with nitrile oxides, nitrile ylides and nitrilimines : An unexpected 1,2,4-triazole formation. / Hemming, Karl; Luheshi, Abdul Bassett N.; Redhouse, Alan D.; Smalley, Robert K.; Thompson, J. Robin; Kennewell, Peter D.; Westwood, R.

In: Tetrahedron, Vol. 49, No. 20, 01.01.1993, p. 4383-4408.

Research output: Contribution to journalArticle

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