DIFFERENT PATHWAYS IN THE BASE-PROMOTED ISOMERIZATION OF BENZYL OXIRANYL ETHERS

Authors
MORDINI A BINDI S PECCHI S DEGLINNOCENTI A REGINATO G SERCI A
Citation
A. Mordini et al., DIFFERENT PATHWAYS IN THE BASE-PROMOTED ISOMERIZATION OF BENZYL OXIRANYL ETHERS, Journal of organic chemistry, 61(13), 1996, pp. 4374-4378
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
13
Year of publication
1996
Pages
4374 - 4378
Database
ISI
SICI code
0022-3263(1996)61:13<4374:DPITBI>2.0.ZU;2-B
Abstract
The base-promoted isomerization of benzyl oxiranyl ethers was investig ated. In particular it was shown that the reaction may proceed toward two main regioisomeric products: a benzyl vinyl ether or a 2-aryl-3-(h ydroxyalkyl)oxetane, depending on subtle variations in the substitutio n on the phenyl ring. Disubstituted oxetanes were obtained in a stereo selective manner, thus providing a good entry to this class of synthet ically useful compounds.