Halonium ion-assisted deiodination of styrene-based vicinal iodohydrins followed by rearrangement through phenyl migration.
J Org Chem
; 74(20): 7947-50, 2009 Oct 16.
Article
de En
| MEDLINE
| ID: mdl-19764730
ABSTRACT
Acid activation of bromate/bromide couple at 0-10 degrees C was found to trigger the deiodination of styrene-based vicinal iodohydrins. Violet coloration of the organic layer was ascribed to formation of IBr. Deiodination was followed by phenyl migration and deprotonation leading to formation of phenyl acetone and 2-phenylpropanal in good yields from 1-iodo-2-phenylpropan-2-ol and 2-iodo-1-phenylpropan-1-ol, respectively. Phenyl acetaldehyde--which was obtained in 92% GC yield from styrene iodohydrin--was also presumably formed in analogous manner. NBS and HOCl too were effective for transformation of styrene iodohydrin into phenyl acetaldehyde.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Langue:
En
Journal:
J Org Chem
Année:
2009
Type de document:
Article
Pays d'affiliation:
Inde