Siliranes: Formation, isonitrile insertions, and thermal rearrangements

被引:36
作者
Kroke, E
Willms, S
Weidenbruch, M
Saak, W
Pohl, S
Marsmann, H
机构
[1] UNIV OLDENBURG,FACHBEREICH CHEM,D-26111 OLDENBURG,GERMANY
[2] UNIV GESAMTHSCH PADERBORN,FACHBEREICH CHEM,D-33095 PADERBORN,GERMANY
关键词
D O I
10.1016/0040-4039(96)00650-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The siliranes 7-10 and 22 as well as the vinylsiliranes 14-16, 20, and 21 are prepared by [1+2]-cycloadditions of silylene 2 with alkenes and dienes. The first isonitrile insertion products, the silacyclobutanimines 26-28 were synthesized and the structure of 28 was determined by X-ray crystallography. Upon thermolysis 20-22 rearranged quantitatively to furnish the compounds 29-32. Copyright (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:3675 / 3678
页数:4
相关论文
共 12 条
[1]   REACTIVITY OF A SILANEDIYL TOWARDS NITRILES - THE ROLE OF AZASILACYCLOPROPENES AS INTERMEDIATES [J].
BELZNER, J ;
IHMELS, H ;
NOLTEMEYER, M .
TETRAHEDRON LETTERS, 1995, 36 (45) :8187-8190
[2]   SYNTHESES, STRUCTURES, AND REACTIONS OF SULFUR AND SELENIUM INSERTION PRODUCTS OF 1,1-DI-TERT-BUTYLSILIRANES [J].
BOUDJOUK, P ;
BLACK, E ;
KUMARATHASAN, R ;
SAMARAWEERA, U ;
CASTELLINO, S ;
OLIVER, JP ;
KAMPF, JW .
ORGANOMETALLICS, 1994, 13 (09) :3715-3727
[3]   SYNTHESIS OF 1,1-DI-TERT-BUTYLSILIRANE, THE 1ST SILIRANE WITH NO SUBSTITUENTS ON THE RING CARBONS [J].
BOUDJOUK, P ;
BLACK, E ;
KUMARATHASAN, R .
ORGANOMETALLICS, 1991, 10 (07) :2095-2096
[4]  
Boudjouk P., 1988, ANGEW CHEM, V100, P1406
[5]   REACTIONS OF A DISILENE AND A SILYLENE WITH CYCLOPENTADIENE, FURAN, AND THIOPHENE - [2+4]-CYCLOADDITIONS VERSUS CHALCOGEN ABSTRACTION [J].
KROKE, E ;
WEIDENBRUCH, M ;
SAAK, W ;
POHL, S ;
MARSMANN, H .
ORGANOMETALLICS, 1995, 14 (12) :5695-5699
[6]  
MARSMANN H, 1981, NMR-BASIC PRINC PROG, V17, P65
[7]   HEXAMETHYLSILIRANE .5. CONVERSION TO 5-MEMBERED RING SILICON-COMPOUNDS BY 2-ATOM INSERTION REACTIONS OF ARYL OLEFINS, 1,3-DIENES, AND CONJUGATED ACETYLENES [J].
SEYFERTH, D ;
DUNCAN, DP ;
SHANNON, ML ;
GOLDMAN, EW .
ORGANOMETALLICS, 1984, 3 (04) :574-578
[8]   HEXAMETHYLSILIRANE .1. PREPARATION, CHARACTERIZATION AND THERMAL-DECOMPOSITION [J].
SEYFERTH, D ;
ANNARELLI, DC ;
VICK, SC ;
DUNCAN, DP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 201 (01) :179-195
[9]   HEXAMETHYLSILIRANE .6. CONVERSION TO 1-OXA-2-SILACYCLOPENTANES BY 2-ATOM INSERTION REACTIONS OF ALDEHYDES AND KETONES [J].
SEYFERTH, D ;
DUNCAN, DP ;
SHANNON, ML .
ORGANOMETALLICS, 1984, 3 (04) :579-583
[10]   DISILENE AND SILYLENE ADDITIONS TO THE DOUBLE-BONDS OF ALKENES AND 1,3-DIENES - MOLECULAR-STRUCTURE OF A [2+2] CYCLOADDITION PRODUCT [J].
WEIDENBRUCH, M ;
KROKE, E ;
MARSMANN, H ;
POHL, S ;
SAAK, W .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (10) :1233-1234