1,7-ACETAL CARBON REARRANGEMENT VIA 1,5-HYDRIDE TRANSFER IN AN OXOCANYL CARBENIUM ION - CONVERSION OF O-(5-HEXENYL)-SE,O-HETEROACETALS OR O,O-ACETALS INTO 7-OXOHEXANOLS OR 7-OXOHEXYL CHLORIDES
M. Yoshimatsu et al., 1,7-ACETAL CARBON REARRANGEMENT VIA 1,5-HYDRIDE TRANSFER IN AN OXOCANYL CARBENIUM ION - CONVERSION OF O-(5-HEXENYL)-SE,O-HETEROACETALS OR O,O-ACETALS INTO 7-OXOHEXANOLS OR 7-OXOHEXYL CHLORIDES, Chemistry Letters, (9), 1993, pp. 1491-1494
Oxacyclooctyl (oxocanyl) carbenium ions generated by treatment of O-(5
-hexenyl)-Se,O-heteroacetals or O,O-acetals with SnCl4 underwent intra
molecular 1,5-hydride transfer, and the alpha-oxy carbenium ions newly
formed were hydrolyzed to give the 7-oxohexanols or 7-oxohexyl chlori
des in good yields. Various O-(5-hexenyl)-Se,O-heteroacetals or O,O-ac
etals were converted into 7-oxohexanols or 7-oxohexyl chlorides.