Bicyclo [3.3. 1] nonanes. II. Synthesis and reactions of simple derivatives

JP Schaefer, JC Lark, CA Flegal…

Index: Schaefer,J.P. et al. Journal of Organic Chemistry, 1967 , vol. 32, p. 1372 - 1378

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Citation Number: 22

Abstract

The preparation of numerous bicyclo [3.3. l] nonane derivatives from available starting materials is described. Conversion of 2-N-morpholinobicyclo [3.3. l] nonan-9-one (2) to 2-N- morpholinobicyclo [3.3. llnonane (3) and reaction of the latter with hydrogen peroxide gave the N-oxide 4 which on pyrolysis produced bicyclo [3.3. l] non-2-ene (5) in good over-all yield. Hydroboration of 5 gave a 2: 3 mixture of ezo-bicyclo [3.3. 1] nonan-2-ol (6) and ezo- ...