Tetrahedron

N-Chloro-N, N′, N′-tris (ethoxycarbonyl) hydrazine and N, N-dichloro-N′, N′-bis (ethoxycarbonyl) hydrazine: synthesis, stability and reactions with nucleophiles

V Benin, P Kaszynski, JG Radziszewski

Index: Benin, Vladimir; Kaszynski, Piotr; George Radziszewski Tetrahedron, 2002 , vol. 58, # 11 p. 2085 - 2090

Full Text: HTML

Citation Number: 4

Abstract

N-Chloro-N, N′, N′-tris (ethoxycarbonyl) hydrazine (1b) was prepared in 27% yield by chlorination of N, N, N′-tris (ethoxycarbonyl) hydrazine anion with t-BuOCl. The reaction of 1b with CN (−) gave the product of N-substitution. Attempts at chlorination of N, N-bis (ethoxycarbonyl) hydrazine (2a) with t-BuOCl did not yield the expected N, N-dichloro-N′, N′-bis (ethoxycarbonyl) hydrazine (1a), and led to the exclusive formation of ClCOOEt. ...