Efficient Synthesis of Selenocarbonyl Compounds by Treating Carbonyl Compounds with Bis (1, 5-cyclooctanediylboryl) Selenide.

K Shimada, N Jin, M Kawaguchi, K Dobashi…

Index: Shimada, Kazuaki; Jin, Norikazu; Kawaguchi, Michiko; Dobashi, Kumiko; Nagano, Yumi; Fujimura, Manabu; Kudoh, Eiichi; Kai, Tomonari; Saito, Noboru; Masuda, Jun-Ichi; Iwaya, Masaki; Fujisawa, Hiroyuki; Aoyagi, Shigenobu; Takikawa, Yuji Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 1 p. 197 - 206

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Citation Number: 24

Abstract

Selenoaldehydes and selenoketones were generated in situ, by treating aldehydes or ketones, respectively, with bis (1, 5-cyclooctanediylboryl) selenide; the resulting selenocarbonyl compounds were trapped with 2, 3-dimethyl-1, 3-butadiene to give the corresponding [4+ 2] cycloadducts. The treatment of amides, an ester, and ketones possessing bulky substituents with the reagent also afforded the corresponding ...