Highly Efficient Formation of Nitriles and Alkoxy Radicals from N-Alkoxybenziminoyl Chlorides in Solution

HJP de Lijser, CR Burke, J Rosenberg…

Index: De Peter Lijser; Burke, Cassandra R.; Rosenberg, Jonathan; Hunter, Jordan Journal of Organic Chemistry, 2009 , vol. 74, # 4 p. 1679 - 1684

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Citation Number: 2

Abstract

A series of N-alkoxybenziminoyl chlorides were synthesized and reacted with tributyltin hydride in the presence of AIBN to generate the corresponding N-alkoxybenziminoyl radicals. This methodology successfully generates the desired radicals, which undergo a rapid and highly efficient β-scission reaction, as shown by the formation of the corresponding nitriles and products derived from alkoxy radicals. The intermediate N- ...