A New Synthetic Route for Silacyclopropanes: Reactions of a Bromosilylenoid with Olefins

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• 作者：Hyeon Mo Cho ; Kyongjin Bok ; Seo Hyeon Park ; Young Mook Lim ; Myong Euy Lee ; Moon-Gun Choi ; Kang Mun Lee
• 刊名：Organometallics
• 出版年：2012
• 出版时间：August 13, 2012
• 年：2012
• 卷：31
• 期：15
• 页码：5227-5230
• 全文大小：207K
• 年卷期：v.31,no.15(August 13, 2012)
• ISSN：1520-6041

文摘

Stable 1-bromo-1-silacyclopropanes were synthesized in high yields from the reaction of the stable bromotrisylsilylenoid 1 (trisyl = C(SiMe₃)₃) with olefins such as styrene, trimethylvinylsilane, triethylvinylsilane, and dimethylphenylvinylsilane, a new synthetic route for silacyclopropanes. The structure of bromosilacyclopropane 5 was confirmed by X-ray analysis. In the presence of excess MeOH the phenyl-substituted bromosilacyclopropane 2 underwent regioselective ring opening to give the corresponding product 6. In contrast, the reaction of silyl-substituted bromosilacyclopropane 5 with MeOH gave only the product of nucleophilic substitution at the silicon atom, 1-methoxy-1-silacyclopropane 7, without any ring opening. Furthermore, the bromosilacyclopropane 2 extruded bromosilylene 8 through a thermal cycloreversion reaction.