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Communication | Regular issue | Vol 6, No. 4, 1977, pp.469-474
Published online, 1st January, 1970
DOI: 10.3987/R-1977-04-0469
Reaction of N-Benzenesulfonyl-9-azabicyclo[3.3.1]nona-2,6-diene with Diborane: Failure of Cyclic Hydroboration in the Intramolecularly Faces Diene System

Takefumi Momose* and Shohgo Atarashi

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

Hydroboration of N-benzenesulfonyl-9-azabicyclo[3.3.1] nona-2,6-diene gave 2,6-diols and exo,exo-2,7-diol in the ratio of ca. 2.3 : 1, but neither exo,exo-3,7-diol nor the products derived from a boraadamantane were formed. A marked site-selectivity in the hydroxylation was discussed in terms of inductive or spatial effects of the N-substituent.