Abstract
Abstract3‐Methoxymorphinan (1) was converted to the corresponding N‐chloro derivative 2 by treatment with aqueous sodium hypochlorite. Upon exposure to methanolic silver nitrate, 2 was rearranged to the carbinolamine ether 3. In addition, considerable amounts of the dechlorinated morphinan 1 were formed. The structure of 3 was secured by spectral analysis and its degradation to the hexahydroindoline derivative 4. The observed skeletal rearrangement of 2 which requires the migration of an alkyl group is discussed in terms of a nitrenium ion.
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