DEAMINATION REACTIONS .56. CYCLOPROPANE PARTICIPATION IN NORBORNYL CATIONS

Nitrous acid deamination of icyclo[2.2.1]heptane-7,1'cyclopropan]-endo -2-amine (13) affords 74% of the analogous endo alcohol 24-OH and 26% of the rearranged exo alcohol 25-OH. The exceptional preference for en do attack of the nucleophile is attributed to intervention of the brid ged norpinyl cation 21 which is stabilized by the spiroannellated cycl opropane ring. The spiro[bicyclo[2.2.1]heptane-3,1'-cyclopropan]-2-yl cations 23 arising from Wagner-Meerwein rearrangement are captured by water to give high exo:endo product ratios.