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1- and 2-Chloromorphine. Halogenation of Morphine meta to the Free Phenolic Hydroxyl Group

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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Abstract

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
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.ernet.in/id/eprint/21892

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