Search for dioxocarbenes in photochemical reactions of 5-diazo-4, 6-dioxo-1, 3-dioxanes, associated diazirines, and S-ylides

VV Shevchenko, NN Khimich, MS Platz, VA Nikolaev

Index: Shevchenko; Khimich; Platz; Nikolaev Tetrahedron Letters, 2005 , vol. 46, # 3 p. 435 - 438

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Citation Number: 9

Abstract

On direct photolysis of 2, 2-dialkyl-5-diazo-4, 6-dioxo-1, 3-dioxanes in the presence of pyridine, methanol or dimethyl sulfide as carbene traps, the yield of 'carbene'products does not exceed 27–28%. At the same time photochemical transformations of the related 3, 3- diacyldiazirines and dioxosulfonium ylides of this series, evidently, occur without generation of carbene intermediates.