Hydroboration of cyclic allenes with disiamylborane
1968; NRC Research Press; Volume: 46; Issue: 15 Linguagem: Inglês
10.1139/v68-431
ISSN1480-3291
AutoresD. S. Sethi, G. C. Joshi, D. Devaprabhakara,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoIt 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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