MISC

2002年9月

Silicon-carbon unsaturated compounds. 66. Photolysis of cis- and trans-1,2-dimethyl-1,2-diphenyl-1,2-disilacyclohexane in the presence of isobutene

ORGANOMETALLICS
  • M Ishikawa
  • ,
  • S Shirai
  • ,
  • A Naka
  • ,
  • H Kobayashi
  • ,
  • J Ohshita
  • ,
  • A Kunai
  • ,
  • Y Yamamoto
  • ,
  • SH Cha
  • ,
  • KK Lee
  • ,
  • YW Kwak

21
20
開始ページ
4206
終了ページ
4211
記述言語
英語
掲載種別
DOI
10.1021/om020316a
出版者・発行元
AMER CHEMICAL SOC

A mixture of cis- and trans-1,2-dimethyl-1,2-diphenyl-1,2-disilacyclohexane (1a and 1b) was prepared by the reaction of 1,4-bis(chloromethylphenylsilyl)butane with lithium metal in the presence of a catalytic amount of dimethylphenylsilyllithium in THF. The photolysis of pure la in the presence of isobutene afforded cis-2,3-benzo-1-isobutyl-1,4-dimethyl-4phenyl-1,4-disilacyclooct-2-ene (2a) in 63% yield, in addition to a small amount of a formal [2 + 2] cycloadduct (3a) with cis-configuration, arising from addition of the rearranged silene with isobutene. Similar photolysis of 1b with isobutene gave a trans-adduct (3b) formed by formal [2 + 21 cycloaddition of the rearranged silene arising from 1b to isobutene as the main product, together with a small amount of trans-2,3-benzo-1-isobutyl-1,4-dimethyl-4phenyl-1,4-disilacyclooct-2-ene (2b). The structure of the [2 + 2] cycloadduct 3b, was verified by X-ray crystallography. The thermolyses of 3a and 3b at 150 degreesC for 24 h produced 2a and 2b, respectively, in quantitative yields.

Web of Science ® 被引用回数 : 8

リンク情報
DOI
https://doi.org/10.1021/om020316a
CiNii Articles
http://ci.nii.ac.jp/naid/80015536111
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000178255000020&DestApp=WOS_CPL

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