Oxidation of 2-phenyl-1-oxa-9-azabicyclo[4.3.0]nonane (5) with m-chloroperoxybenzoic acid is not regioselective, in contrast to the case with the corresponding 1-oxa-8-azabicyclo[3.3.0]octane (2; n= 1, R1= H, R2= Ph), affording mainly the keto-nitrone (7). On reaction with styrene in boiling toluene the latter forms the oxabicyclononane (9).
W. Carruthers, P. Coggins and J. B. Weston, J. Chem. Soc., Chem. Commun., 1990, 91 DOI: 10.1039/C39900000091
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