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Communication | Regular issue | Vol 27, No. 8, 1988, pp.1817-1820
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4589
3-O-(1-Phenyltetrazol-5-yl)morphine in the Acid-catalyzed Morphine-Apomorphine Rrearrangement: Formation of a Side Product Due to 1-Phenyltetrazole Group Migration

Prem Mohan* and Joseph G. Cannon

*Department of Medical Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, P.O.Box 6998, Chicago, IL 60680, U.S.A.


Acid catalyzed rearrangement of the title compound leads to a second aporphine derivative in addition to the expected product, 10-O-(1-phenyltetrazol-5-yl)-apomorphine. This side product is isomeric with the expected product, and it was shown to be 11-O-(1- phenyltetrazol-5-yl)apomorphine, apparently formed by tetrazole ring migration in the course of the acid catalyzed rearrangement of the morphine derivative.