English
往期目录
新闻公告
More
化学进展 2009, Vol. 21 Issue (0708): 1487-1493 前一篇   后一篇

• 综述与评论 •

硅杂六元环化合物的反应*

张韶光;刘俊辉;张文雄;席振峰**   

  1. (北京分子科学国家实验室 生物有机与分子工程教育部重点实验室  |北京大学化学与分子工程学院  |北京市 100871)
  • 收稿日期:2008-10-17 修回日期:2008-11-18 出版日期:2009-08-24 发布日期:2009-06-30
  • 通讯作者: 席振峰 E-mail:zfxi@pku.edu.cn
  • 基金资助:

    国家自然科学基金

下载PDF ( 2670 ) 引用
导出

Reactivity of Six-membered Silacycles

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

  1. (Beijing National Laboratory for Molecular Sciences, MOE Key Laboratory of Bioorganic Chemistry and Molecular Engineering, and College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China)
  • Received:2008-10-17 Revised:2008-11-18 Online:2009-08-24 Published:2009-06-30
  • Contact: Xi Zhenfeng E-mail:zfxi@pku.edu.cn

硅杂六元环化合物在有机硅化学中是一类重要的小分子环系化合物， 广泛应用于有机化学、高分子化学、金属有机化学以及材料化学等领域。本文综述了环上只含有一个硅原子的硅杂六元环化合物的反应，介绍了硅原子上取代基的反应、立体选择性合成、硅原子α-位碳原子上的反应、插入反应、环加成反应、Si-C键的切断反应、硅杂苯衍生物合成以及金属配位反应等，并展望了硅杂六元环化合物反应化学的发展方向。

关键词： 硅杂环己烷, 硅杂环己烯, 硅杂环己二烯, 硅杂苯, 插入反应, 环加成反应

Six-membered silacycles are a class of important cyclic compounds in organosilicon chemistry, which have many applications in organic chemistry, polymer chemistry, organometallic chemistry and materials science. Eight kinds of reactions of six-membered silacycles with one silicon atom in the ring are mainly included in this review. They are reactions at the substituent on the silicon atom, stereoselective organic transformations, reactions at the α-position of silicon atom, insertion reactions, cycloadditions, Si-C bond cleavage reactions, formation of silabenzene derivatives and metal coordination reactions. The prospects of reactivity and synthetic application of six-membered silacycles are also included in the review.

Contents
1 Introduction
2 Reactions at the substituent on the silicon atom
3 Stereoselective organic transformations
4 Reactions at the α-position of silicon atom
5 Insertion reactions
6 Cycloadditions
7 Si-C bond cleavage reactions
8 Formation of silabenzene derivatives
9 Metal coordination reactions
10 Prospects

Key words: silacyclohexane, silacyclohexene, silacyclohexadiene, silabenzene, insertion reaction, cycloaddition

中图分类号: 

()

[ 1 ] 　Hermanns J , Schmidt B. J . Chem. Soc. Perkin Trans. 1 , 1999 ,81 —102
[ 2 ] 　Franz A K, Woerpel KA. Acc. Chem. Res. , 2000 , 33 : 813 —820
[ 3 ] 　Murakami S , Ito Y. Topics in Organometallic Chemistry. Berlin :Springer-Verlag , 1999. 97
[ 4 ] 　Brook M A. Silicon in Organic , Organometallic, and Polymer Chemistry. New York : John Wiley &Sons , 2000. 522
[ 5 ] 　Mohseni-Ala J , Auner N. Inorganica Chimica Acta , 2006 , 359 :4677 —4697
[ 6 ] 　Michl J . Chem. Rev. , 1995 , 95 (5) : 1135 —1135
[ 7 ] 　Sakurai H , Murakami M. Bull . Chem. Soc. Jpn. , 1976 , 49 :3185 —3189
[ 8 ] 　Sakurai H , Murakami M. Bull . Chem. Soc. Jpn. , 1977 , 50 :3384 —3387
[ 9 ] 　Rendler S , Oestreich M, Butts C P , Jones G C L. J . Am. Chem.Soc. , 2007 , 129 (3) : 502 —503
[10 ] 　Negron A , Soderquist J A. Tetrahedron Lett . , 1998 , 39 ( 51) :9397 —9400
[11 ] 　Hughes N J , Pullin R D C , Sanganee MJ , Sellars J D , Steel P G,Turner MJ . Org. Biomol . Chem. , 2007 , 5 (17) : 2841 —2848
[12 ] 　Berry MB , Griffiths RJ , Sanganee MJ , Steel P G, Whelligan D K.Tetrahedron Lett . , 2003 , 44 (51) : 9135 —9138
[13 ] 　Pullin R D C , Sellars J D , Steel P G. Org. Biomol . Chem. , 2007 ,5 (19) : 3201 —3206
[14 ] 　Barton TJ , Banasiak D S. J . Organomet . Chem. , 1978 , 157 (3) :255 —266
[15 ] 　Hoshino O , Taguchi T, Miyauchi K, Tatsuno A. Heterocycles ,1995 , 40 : 975 —982
[16 ] 　Sakurai H , Murakami M. J . Am. Chem. Soc. , 1972 , 94 (14) :5080 —5082
[17 ] 　Seyferth D , Washburne S S. J . Organomet . Chem. , 1966 , 5 (4) :389 —391
[18 ] 　Seyferth D , Washburne S S , Attridge C J , Yamamoto K. J . Am.Chem. Soc. , 1970 , 92 (14) : 4405 —4417
[19 ] 　Nakadaira Y, Sato R , Sakurai H. Organometallics , 1991 , 10 (2) :435 —442
[20 ] 　Damour D , Barreau M, Fardin V , Dhaleine F , Vuilhorgne M,Mignani S. Synlett , 1998 , 153 —156
[21 ] 　Maier G, Mihm G, Reisenauer H P. Angew. Chem. , 1981 , 93 :615 —616
[22 ] 　Conlin R T, Kwak YW. Organometallics , 1984 , 3 : 918 —922
[23 ] 　Auner N , Steinberger H U. Z. Naturforsch. Teil B , 1994 , 49 :1743 —1754
[24 ] 　Steinmetz M G, Seguin KJ , Udayakumar B S , Behnke J S. J . Am.Chem. Soc. , 1990 , 112 : 6601 —6608
[25 ] 　Steinmetz M G, Yu C. J . Org. Chem. , 1992 , 57 : 3107 —3120
[26 ] 　Badali F , Karalis A , Tham W Y, White J M. Aust . J . Chem. ,1996 , 49 : 1293 —1299
[27 ] 　Barton T J , Vuper M. J . Am. Chem. Soc. , 1981 , 103 ( 22) :6788 —6789
[28 ] 　Wakita K, Tokitoh N , Okazaki R , Takagi N , Nagase S. Angew.Chem. Int . Ed. , 2000 , 39 (3) : 634 —636
[29 ] 　Wakita K, Tokitoh N , Okazaki R , Takagi N , Nagase S. J . Am.Chem. Soc. , 2000 , 122 (23) : 5648 —5649
[30 ] 　Tokitoh N , Wakita K, Okazaki R , Nagase S , Schleyer P R , Jiao H.J . Am. Chem. Soc. , 1997 , 119 (29) : 6951 —6952
[31 ] 　Takeda N , Shinohara A , Tokitoh N. Organometallics , 2002 , 21(20) : 4024 —4026
[32 ] 　Takeda N , Shinohara A , Tokitoh N. Organometallics , 2002 , 21 (2) :256 —258
[33 ] 　Tokitoh N , Shinohara A , Matsumoto T, Sasamori T, Takeda N ,Furukawa Y. Organometallics , 2007 , 26 (16) : 4048 —4053
[34 ] 　Afanasova O B , Chernyshev E A , Gudkova N G, Strelenko Y A ,Nosova V M, Nikol'skii A A. Zhurnal Obshchei Khimii , 1985 , 55 :925 —929
[35 ] 　Shinohara A , Takeda N , Sasamori T, Matsumoto T, Tokitoh N.Organometallics , 2005 , 24 : 6141 —6146
[1] 曹如月, 肖晶晶, 王伊轩, 李翔宇, 冯岸超, 张立群. 杂Diels-Alder 环加成反应级联RAFT聚合[J]. 化学进展, 2023, 35(5): 721-734.
[2] 董军, 许家喜. 烯亚砜化合物的制备及反应概述[J]. 化学进展, 2022, 34(5): 1088-1108.
[3] 廖伊铭, 吴宝琪, 唐荣志, 林峰, 谭余. 环张力促进的叠氮-炔环加成反应[J]. 化学进展, 2022, 34(10): 2134-2145.
[4] 章强, 黄文峻, 王延斌, 李兴建, 张宜恒. 基于铜催化叠氮-炔环加成反应的聚氨酯功能化[J]. 化学进展, 2020, 32(2/3): 147-161.
[5] 方德彩*. [2+2]环加成反应机理的理论研究[J]. 化学进展, 2012, 24(06): 879-885.
[6] 杨绳岩, 吴振奕, 万新军, 晏娟. 卟啉-富勒烯络合物的合成[J]. 化学进展, 2011, 23(6): 1123-1136.
[7] 王春,刘伟华,周欣,李越敏,李云鹏. 有机催化不对称[4+2]环加成反应*[J]. 化学进展, 2009, 21(09): 1857-1868.
[8] 刘俊辉,张韶光,张文雄,席振峰. 硅杂六元环化合物的合成*[J]. 化学进展, 2009, 21(0708): 1475-1486.
[9] 方钊,唐瑞仁,罗佐文. 烯酮中间体及其在不对称环加成反应中的应用[J]. 化学进展, 2008, 20(10): 1544-1552.
[10] 王钦 李玫 余孝其 谢如刚. 金属配合物催化氮杂环丙烷化和饱和C —H键氮插入反应*[J]. 化学进展, 2005, 17(02): 275-285.
[11] 许家喜,焦鹏. 固相载体上的环加成反应及其应用[J]. 化学进展, 2000, 12(02): 131-.
阅读次数
全文


摘要

硅杂六元环化合物的反应*