Hydroboration of cyclic allenes with disiamylborane

Sethi, D. S. ; Joshi, G. C. ; Devaprabhakara, D. (1968) Hydroboration of cyclic allenes with disiamylborane Canadian Journal of Chemistry, 46 (15). pp. 2632-2634. ISSN 0008-4042

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Related URL: http://dx.doi.org/10.1139/v68-431


It has been shown that 1,2-cyclononadiene and 1,2-cyclotridecadiene undergo 78 and 100% hydroboration respectively, with disiamylborane. 1,2-Cyclononadiene gave products which represented 83% attack of boron at the central carbon atom and 17% attack at the terminal carbon atom. 1,2-Cyclotridecadiene gave 62% central carbon attack and 38% terminal carbon attack. The reactivity and selectivity may be explained mainly in terms of steric effects on a four-centered transition state.

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