European journal of organic chemistry

First propargyl azides bearing strong acceptor substituents and their effective conversion into allenyl azides: influence of the electronic effects of substituents on the …

JR Fotsing, K Banert

Index: Fotsing, Joseph Rodolph; Banert, Klaus European Journal of Organic Chemistry, 2005 , # 17 p. 3704 - 3714

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Citation Number: 14

Abstract

Abstract We have succeeded in the synthesis of propargyl azides containing 1-or 3- phenylthio functionalities. The selective oxidation of their sulfur atoms to sulfoxides and sulfones allows access to the first propargyl azides bearing acceptor substituents. Interestingly, the prototropic rearrangement of the latter propargyl azides leads to the formation of allenyl azides with relatively high stabilities and with moderate to good yields. ...