Singh, Bajrang Bali and Chauhan, Ranjit Singh and Madyastha, Kattigari Madhava and Bhatnagar, Surendra P and Kirk, Kenneth L and Weiss, Ulrich (1982) 1- and 2-Chloromorphine. Halogenation of Morphine meta to the Free Phenolic Hydroxyl Group. In: Heterocycles, 19 (5). pp. 837-847.
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Treatment of morphine in aqueous HCl at 70° with KIO3 yields a monochloromorphine, identified as 1-chloromorphine by spectroscopic means and by the fact that it, and its methyl ether 1-chlorocodeine, are different from 2-chloromorphine and 2-chlorocodeine prepared from 2-aminomorphine of unequivocally established structure. Formation of 1-chloromorphine and the previously known 1-bromomorphine involves entry of the halogen into the position meta to the free phenolic hydroxyl. Possible mechanistic interpretations of this unusual orientation are discussed.
| Item Type: | Journal Article |
|---|---|
| Publication: | Heterocycles |
| Publisher: | Japan Institute of Heterocyclic Chemistry |
| Additional Information: | Copyright of this article belongs to Japan Institute of Heterocyclic Chemistry. |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 29 Jul 2009 02:49 |
| Last Modified: | 29 Jul 2009 02:49 |
| URI: | http://eprints.iisc.ac.in/id/eprint/21892 |
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