Journal of the American Chemical Society

Nature of the carbonium ion. X. 2-Protoadamantyl cation

LA Spurlock, KP Clark

Index: Spurlock,L.A.; Clark,K.P. Journal of the American Chemical Society, 1972 , vol. 94, # 15 p. 5349 - 5360

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Citation Number: 21

Abstract

Results Bicyclo [3.2. l] oct-6-en-3-one (1) was prepared through the ring expansion of norbornadiene by the methods of Moore, Moser, and La Prade6 and LeBel and Liesemer. 7 Reduction of 1 with a large excess of sodium in ethanol afforded a mixture of exo-and endo- bicyclo [3.2. l] oct-6-en-3-01s (see Scheme I). 8 Analysis of the alcohol mixture by gc showed it to be 95% 2a and 5% of its endo epimer.