Effect of Remote Substitution on Face Selection in Addition Reactions of Nor-and Homoadamantan-9-ones and of Several Analogues

M Kaselj, EM Gonikberg…

Index: Kaselj, Mira; Gonikberg, Elena M.; Le Noble, William J. Journal of Organic Chemistry, 1998 , vol. 63, # 10 p. 3218 - 3223

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Citation Number: 13

Abstract

The effects of 3-halo substitution on face selection in borohydride reductions of both nor-and homoadamantan-9-ones 1-X and 3-X, respectively, have been compared with those of 5- halo substitution in the parent 5-haloadamantan-2-ones 2-X. The differences between the product ratios in these three compounds are small, but the selectivity of 2-X is somewhat larger than that of either of the homologues. This is also true of the corresponding aza-and ...