Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)benzothiazoles by the Reaction Involving Se -> O Azaaromatic Ring Rearrangement

Article abstract of DOI:10.1246/bcsj.65.3163

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-pentenyl 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.