A thio-staudinger reaction: Thermolysis of a vinyl azide in the presence of t-butyl mercaptan

RR Sauers, SD Van Arnum

Index: Sauers, Ronald R.; Van Arnum, Susan D. Phosphorus, Sulfur and Silicon and the Related Elements, 2003 , vol. 178, # 10 p. 2169 - 2181

Full Text: HTML

Citation Number: 10

Abstract

The thermal decomposition of E-3-azido-3-hexene-2, 5-dione (1) in protic media gave rise to several novel reactions of the azide 1 including adducts derived from keteneimine 11. Reaction with t-butyl mercaptan yielded two products, keteneimine-derived mercaptan addition product 20 and a sulfenimine 6. Trapping of a vinyl nitrene intermediate or a thio- Staudinger reaction was considered as a possible mechanism for the formation of ...