Hydroboration of acyclic allenes with disiamylborane

Sethi, D. S. ; Joshi, G. C. ; Devaprabhakara, D. (1969) Hydroboration of acyclic allenes with disiamylborane Canadian Journal of Chemistry, 47 (6). pp. 1083-1086. ISSN 0008-4042

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Related URL: http://dx.doi.org/10.1139/v69-172


The present investigation demonstrates the hydroboration of 1,2-nonadiene, phenylpropadiene, 3-phenyl-1,2-butadiene, 4,5-nonadiene, and tetramethylallene with disiamylborane. All the allenes except tetramethylallene underwent 100% conversion. Examination of the products indicated preferential electrophilic attack of boron on the least substituted terminal carbon atom in the case of 1,2-nonadiene, phenylpropadiene, 3-phenyl-1,2-butadiene, and on the central carbon atom in 4,5-nonadiene. In tetramethylallene boron, attack was exclusively on the central carbon atom. These results have been explained in terms of steric effects on a four-centered transition state.

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