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Skeletal Rearrangement of 3-Methoxy-N-chloromorphinan
Mohacsi, E.,Hayes T.
, p. 901 - 903 (2007/10/02)
3-Methoxymorphinan (1) was converted to the corrsponding N-chloro derivative 2 by tratment 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 netrenium ion.
