Tetrahedron

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.

K Hemming, ABN Luheshi, AD Redhouse, RK Smalley…

Index: Hemming, Karl; Luheshi, Abdul-Bassett N.; Redhouse, Alan D.; Smalley, Robert K.; Thompson, J. Robin; et al. Tetrahedron, 1993 , vol. 49, # 20 p. 4383 - 4408

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Citation Number: 16

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 ...