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Paper | Special issue | Vol 50, No. 2, 1999, pp.731-738
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)69
A Radical Route to Morphans. Synthesis and Spectroscopic Data of the 2-Azabicyclo-[3.3.1]nonane

Josefina Quirante, Carmen Escolano, Faïza Diaba, and Josep Bonjoch*

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain


The synthesis of 1-benzyl-2-azabicyclo[3.3.1]nonan-3-one (8) through radical cyclization, involving an intramolecular addition of a carbamoyl-dichlomethyl radical upon an alkene, is described. Conversion of 8 to the morphan itself, and the spectroscopic analysis of some derivatives of this series are reported.