Journal Article Spontaneous Oxygenation of Siloxy-N-silylketenimines to α-Ketoamides

Sasaki, Michiko  ,  Ando, Masafumi  ,  Kawahata, Masatoshi  ,  Yamaguchi, Kentaro  ,  Takeda, Kei

18 ( 7 )  , pp.1598 - 1601 , 2016-04-01 , American Chemical Society
Siloxy-N-silylketenimines generated in situ from Osilyl cyanohydrins were converted to α-ketoamides by brief exposure to air or oxygen. Oxidation under extremely mild conditions can be explained by assuming the intermediacy of a 3-imino-1,2-dioxetane derivative generated via triplet−singlet intersystem crossing after the reaction of siloxy-N-silylketenimines with triplet oxygen.
This research was partially supported by a Grant-in-Aid for Scientific Research (C) 25460015 (M.S.), a Grant-in-Aid for Challenging Exploratory Research 15K14929 (K.T.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), the Hoan Sha Foundation (M.S.), the Takeda Science Foundation (M.S.), and the Naito Foundation Natural Science Scholarship (M.S.).

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