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.Full text not available from this repository. (Request a copy)
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|
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