Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)benzothiazoles by the Reaction Involving Se → O Azaaromatic Ring Rearrangement
作者:Koichi Shibata、Oyo Mitsunobu
DOI:10.1246/bcsj.65.3163
日期:1992.11
The reactions of 2-(2-oxoalkylseleno)benzothiazoles with allylic Grignard reagents in the presence of BF3·OEt2 gave the corresponding 2-[(2-alkyl-2-hydroxy-4-pententyl or 2-alkyl-2-hydroxy-4-methyl-4-pentenyl)seleno]benzothiazoles which, on treatment with Ph3P and NaH, afforded 1,4-dienes in good to excellent yields.
Allylic gallium sesquibromides prepared by reduction of allylic bromides with gallium metal in the presence of a catalytic amount of indium, add to terminal alkynes with the aid of a tertiaryamine to give 1,4-dienes.