Rearrangements of azidoquinones. XVI. Thermal and photolytic rearrangements of 2, 5-diazido-1, 4-quinones. Synthesis and chemistry of cyanoketenes

W Weyler Jr, WG Duncan…

Index: Weyler,W. et al. Journal of the American Chemical Society, 1975 , vol. 97, p. 6187 - 6192

Full Text: HTML

Citation Number: 29

Abstract

Abstract: 2, 5-Diazido-and 2, 6-diazido-1, 4-quinones undergo a unique thermal cleavage to cyanoketenes. This fragmentation proceeds in two distinct stages. The first is a ring contraction to 4-azido-2-cyano-4-cyclopentene-l, 3-diones, and the second is the cleavage of these intermediates to two molecules of the corresponding cyanoketenes. This reaction is particularly useful for the synthesis of tert-butyl-and tert-pentylcyanoketene which ...