Addition of trimethylsilyl azide and of “mixed anhydrides” to the N??C (3) σ??bond in 3??substituted??1??azabicyclo [1.1. 0] butanes

…, GVM Sharma, D Rajagopal, R Shukla…

Index: Marchand, Alan P.; Sharma; Rajagopal; Shukla, Rajesh; Mloston, Grzegorz; Bartnik, Romuald Journal of Heterocyclic Chemistry, 1996 , vol. 33, # 3 p. 837 - 840

Full Text: HTML

Citation Number: 8

Abstract

Abstract Trimethylsilyl azide adds smoothly to the highly strained NC (3) σ-bond in 3-ethyl-1- azabicyclo [1.1. 0]-butane (1) to afford an adduct, 2, that reacts in situ with a variety of electrophilic reagents (ie., ethyl chloroformate, p-toluenesulfonyl chloride, benzoyl chloride, acetyl chloride, and oxalyl chloride) to afford the corresponding N-substituted-3-azido-3- ethylazetidines 3–7, respectively in 62–72% yield. Similarly, 1 reacts regiospecifically with ...