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

Authors
YOSHIMATSU M HATAE N SHIMIZU H KATAOKA T
Citation
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
Citations number
5
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
9
Year of publication
1993
Pages
1491 - 1494
Database
ISI
SICI code
0366-7022(1993):9<1491:1CRV1T>2.0.ZU;2-5
Abstract
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.