Chemistry of diazocarbonyl compounds: XXV. Comparative photochemistry of diazo compounds and sulfur ylides of the 1, 3-dioxane-4, 6-dione series

VA Nikolaev, VV Shevchenko, MS Platz…

Index: Nikolaev; Shevchenko; Platz; Khimich Russian Journal of Organic Chemistry, 2006 , vol. 42, # 6 p. 815 - 827

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Citation Number: 19

Abstract

Abstract Photochemical decomposition of 2, 2-dialkyl-5-diazo-1, 3-dioxane-4, 6-diones in the presence of pyridine, methanol, or dimethyl sulfide as carbene traps involves mainly the Wolff rearrangement which is likely to follow a concerted pattern, while the yield of the “carbene” products does not exceed 27–28%. No carbene intermediates are formed in the photolysis of the corresponding dioxo sulfonium ylides under analogous conditions, and ...