PHOTOLYSIS OF ORGANOPOLYSILANES - REACTION OF TRIMETHYLSILYLPHENYLSILYLENE WITH OLEFINS AND CONJUGATED DIENES

被引:55
作者
ISHIKAWA, M
NAKAGAWA, KI
KUMADA, M
机构
[1] Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto
关键词
D O I
10.1016/S0022-328X(00)87864-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The photolysis of tris(trimethylsilyl)phenylsilane (I) in the presence of olefins and dienes has been investigated. Irradiation of I in the presence of 1-butene, cis- and trans-2-butene, isobutene and trimethylvinylsilane with a low-pressure mercury lamp bearing a Vycor filter afforded the respective silacyclopropanes (AC). These compounds could be trapped by methanol as the corresponding methoxysilanes. In no case were alkenyldisilanes, which can be expected from photoisomerization of the silacyclopropanes, observed. Photolysis of silacyclopropanes A and B with a high-pressure mercury lamp afforded a mixture of the silylalkenes arising from both 1,2-and 1,3-hydrogen shift, while that of silacyclopropane C gave no volatile products. Irradiation of I in the presence of 2,3-dimethylbutadiene gave 1-pheyl-1-trimethylsilyl-3,4-dimethyl-1-silacyclopent-3-ene, in addition to methoxysilanes arising from methanolysis of the alkenylsilacyclopropane (D). The reaction of trimethylsilylphenylsilylene with 1,3-cyclooctadiene produced 9-phenyl-9-trimethylsilyl-9-silabicyclo[6.1.0]-nona-2-ene (E) as the sole product. Photolysis of E with a high-pressure mercury lamp having a quartz filter afforded two isomers of 9-phenyl-9-trimethylsilyl-9-silabicyclo [4.2.1]nona-7-ene. © 1979.
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页码:105 / 118
页数:14
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