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Progress in Chemistry 2009, Vol. 21 Issue (0708): 1475-1486 Previous Articles   Next Articles

• Review •

Synthesis of Six-membered Silacycles

Liu Junhui ;  |Zhang Shaoguang ;  |Zhang Wenxiong ;  |Xi Zhenfeng**   

  1. (Beijing National Laboratory for Molecular Sciences, MOE Key Laboratory of Bioorganic Chemistry and Molecular Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China)
  • Received: Revised: Online: Published:
  • Contact: Xi Zhenfeng E-mail:zfxi@pku.edu.cn
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Progress in synthetic methodology for six-membered silacycles with one silicon atom in the ring was introduced. Six-membered silacycles are synthesized by the following methods: ring closure by silylation of α, ω-dimetallic compounds, [4+2] cycloaddition reaction involving silenes, ring closure by C-Si bond formation, ring closure by C-C bond formation, ring expansion reaction of smaller silacycles, etc. A variety of silacyclohexane, silacyclohexene and silacyclohexadiene derivatives are readily accessible by these transformations. Further application of six-membered silacycles in organic chemistry and materials science can be envisioned.

Contents
1 Introduction
2 Ring closure by silylation of α, ω-dimetallic compound
2.1 Silylation of 1,3-dilithium
2.2 Silylation of 1,4-dilithium
2.3 Silylation of 1,5-dimetallic reagent
3 [4+2] cycloaddition reaction involving silenes
4 Ring closure by C-Si bond formation
5 Ring closure by C-C bond formation
5.1 Ring closure mediated or catalyzed by Lewis acid
5.2 Cyclization reaction via organoborane
5.3 Ring formation mediated by transition metal
5.4 Ring closing meathesis(RCM)
6 Ring expansion of smaller silacycles
6.1 Three-membered silacycles
6.2 Four-membered silacycles
6.3 Five-membered silacycles
7 Others
8 Prospects

Key words: silacyclohexane, silacyclohexene, silacyclohexadiene

CLC Number: 

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[1] Zhang Shaoguang Liu Junhui Zhang Wenxiong Xi Zhenfeng. Reactivity of Six-membered Silacycles [J]. Progress in Chemistry, 2009, 21(0708): 1487-1493.
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Abstract

Synthesis of Six-membered Silacycles