The Journal of Organic Chemistry

Enamines of 3, 3-dimethylazetidine

HW Thompson, J Swistok

Index: Thompson, Hugh W.; Swistok, Joseph Journal of Organic Chemistry, 1981 , vol. 46, # 24 p. 4907 - 4911

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Citation Number: 14

Abstract

In an improvement over previous procedures, 3, 3-dimethylazetidine (3) has been synthesized in 26% yield from ethyl cyanoacetate. Rates of formation for the enamines of 3 and of pyrrolidine with 2-methylcyclohexanone (1) and 1-tetralone (2) have been studied. The 5-to 10-fold rate increase observed for 3 is attributed to diminished steric hindrance relative to pyrrolidine. Compared to the enamines of pyrrolidine with 1 and 2, those of 3 ...