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Synthesis 2000; 2000(13): 1819-1821
DOI: 10.1055/s-2000-8233
short paper
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A Novel Regio- and Stereoselective Hydrochlorination Reaction of Acetylenic Selenides; Highly Stereoselective Synthesis of (Z)-1-Chloro-1-seleno-1-enes and Stereodefined Selenoenynes

Aiming Sun* , Xian Huang
  • *Department of Chemistry, Zhejiang University, Xi-xi Campus, Hangzhou 31 00 28, P. R. China; Fax +8 65 71 8 80 70 77; E-mail: xhuang@mail.hz.zj.cn
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Publication Date:
31 December 2000 (online)

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(Z)-1-Chloro-1-seleno-1-enes have been synthesized regio- and stereoselectively by the reaction of lithium chloride in HOAc with acetylenic selenides. In the presence of 5% mmol of PdCl2(PhCN)2 and 10% mmol of CuI, (Z)-1-chloro-1-seleno-1-enes coupled with terminal acetylene rapidly to give selenoenynes in high yields.

acetylenic selenide - lithium chloride - regioselectivity - stereoselectivity - (Z)-1-chloro-1-seleno-1-ene - selenoenyne

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