Various diacyl selenides, diacyl diselenides and selenocarboxylates were synthesized by reaction of several acyl chlorides with LiAlHSeH. Reaction of diacyl chloride with LiAlHSeH afforded cyclic selenoanhydrides. In the 77Se NMR spectra, we found that the chemical shifts of the diacyl selenides and the diacyl diselenides could facilitate their distinction.
Reaction of acylchlorides with phenylselenotrimethylsilane promoted by TBAF afforded a mildgeneral access to selenolesters in good yields. When acylchlorides were reacted with bis(trimethylsilyl)selenide (HMDSS) in 2:1 or 1:1 ratio a selective entry to selenoanhydrides or diacyl diselenides respectively was obtained.
SELENIUM TRANSFER REACTION OF PRIMARY SELENOAMIDES: A NOVEL METHOD FOR THE SYNTHESIS OF DIACYLSELENIDES FROM ACYL CHLORIDES
作者:Hua-Rong Zhao、Xin-Jian Zhao、Xian Huang
DOI:10.1081/scc-120014047
日期:2002.1
ABSTRACT Diacyl selenides were afford in excent yields by reaction of primary selenoamides with acyl chlorides in chloroform. A possible mechanism is discussed.