HYDROBORATION .53. CYCLIC HYDROBORATION OF 1,5-CYCLOOCTADIENE WITH MONOHALOBORANE COMPLEXES - SIMPLE, CONVENIENT SYNTHESIS OF B-HALO-9-BORABICYCLO[3.3.1]NONANES

被引:15
作者
BROWN, HC
KULKARNI, SU
机构
[1] Richard B. Wetherill Laboratory, Purdue University, West Lafayette, Indiana
关键词
D O I
10.1021/jo01328a018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The hydroboration of 1, 5-cyclooctadiene with stable methyl sulfide complexes of monochloro-, monobromo-, and monoiodoboranes (H2BX-SMe2gives a mixture of B-halo-9-borabicyclo[3.3.1]nonane (B-X-9-BBN) and its [4.2.l] isomer. The thermodynamically less stable [4.2.1] isomer predominates in the mixture. This can be readily converted to the more stable isomer B-X-9-BBN by gentle heating. The methyl sulfide complexes are isolated as stable crystalline solids. Distillation, following the addition of 1 equiv of the respective boron trihalide, provides B-X-9-BBN free from SMe2. These compounds have been characterized by physical and chemical means. They exhibit promise as synthetic intermediates. © 1979, American Chemical Society. All rights reserved.
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页码:2422 / 2425
页数:4
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