Agrawal, Manoj K. ; Ghosh, Pushpito K. (2009) Halonium ion-assisted deiodination of styrene-based vicinal iodohydrins followed by rearrangement through phenyl migration Journal of Organic Chemistry, 74 (20). pp. 7947-7950. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo9013707
Related URL: http://dx.doi.org/10.1021/jo9013707
Abstract
Acid activation of bromate/bromide couple at 0-10 °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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 60287 |
| Deposited On: | 08 Sep 2011 13:28 |
| Last Modified: | 08 Sep 2011 13:28 |
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