PHOTOCHEMICALLY GENERATED SILICON-CARBON DOUBLE-BONDED INTERMEDIATES .10. PHOTO-CHEMICAL BEHAVIOR OF 1-DISILANYLNAPHTHALENES AND 2-DISILANYLNAPHTHALENES

被引:34
作者
ISHIKAWA, M [1 ]
ODA, M [1 ]
MIYOSHI, N [1 ]
FABRY, L [1 ]
KUMADA, M [1 ]
YAMABE, T [1 ]
AKAGI, K [1 ]
FUKUI, K [1 ]
机构
[1] KYOTO UNIV,FAC ENGN,DEPT HYDROCARBON CHEM,KYOTO 606,JAPAN
关键词
D O I
10.1021/ja00510a028
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The photolysis of 1-pentamethyldisilanyl-, 1-(1ʹ-phenyltetramethyldisilanyl)-, and 1-(2ʹ-phenyltetramethyldisilanyl)naphthalene and 2-pentamethyldisilanyl-and 2-(2ʹ-phenyltetramethyldisilanyl)naphthalene has been investigated. Irradiation of 1-disilanylnaphthalenes in the presence or absence of a trapping agent afforded isomers, 1-hydrosilyl-2-silylnaphthalenes, via photochemical formation of the silicon-carbon double-bonded intermediate, followed by an intramolecular 1, 3-hydrogen shift. From photolysis of 2-disilanylnaphthalenes in the presence of a trapping agent, however, addition products, which could be formed from the reaction of the unsaturated silicon species with the trapping agent, were obtained. The CNDO/2 calculations have been carried out on 1-perhydrodisilanyl-and 2-perhydrodisilanylnaphthalene and also on the silicon-carbon double-bonded intermediates produced from the disilane derivatives. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:4612 / 4618
页数:7
相关论文
共 25 条
[1]   ELECTRICAL EFFECTS IN THE BIPHENYL AND NAPHTHALENE SYSTEMS - THE INFLUENCE OF ALKYL GROUPS ATTACHED TO SILICON ON DESILYLATION REACTIONS [J].
BENKESER, RA ;
SCHROEDER, W ;
THOMAS, OH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (09) :2283-2287
[2]   THEORETICAL-STUDY OF MULTIPLE BONDING IN CARBON AND SILICON [J].
BLUSTIN, PH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 105 (02) :161-168
[3]   UNSTABLE SILICON ANALOGS OF UNSATURATED-COMPOUNDS [J].
GUSELNIKOV, LE ;
NAMETKIN, NS ;
VDOVIN, VM .
ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (01) :18-25
[4]   PHOTOCHEMICALLY GENERATED SILICON-CARBON DOUBLE-BONDED INTERMEDIATES .6. REACTION OF PHENYL AND PARA-TOLYLPENTAMETHYLDISILANES WITH ALKYNES [J].
ISHIKAWA, M ;
FUCHIKAMI, T ;
KUMADA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 127 (02) :261-272
[5]  
ISHIKAWA M, 1977, J CHEM SOC CHEM COMM, P352
[6]   PHOTOCHEMICALLY GENERATED SILICON-CARBON DOUBLE-BONDED INTERMEDIATES .4. PHOTOLYSIS OF 1-ALKENYLDISILANES [J].
ISHIKAWA, M ;
FUCHIKAMI, T ;
KUMADA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 117 (03) :C58-C62
[7]   CHEMISTRY OF A 1-SILACYCLOPROPENE - THERMAL PRODUCTION OF 1,4-DISILACYCLOHEXA-2,5-DIENES [J].
ISHIKAWA, M ;
FUCHIKAMI, T ;
KUMADA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 142 (03) :C45-C48
[8]   PHOTOLYSIS OF ORGANOPOLYSILANES - FORMATION AND REACTIONS OF SUBSTITUTED 1-SILACYCLOPROPENE AND 1-SILA-1,2-PROPADIENE [J].
ISHIKAWA, M ;
FUCHIKAMI, T ;
KUMADA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (01) :245-247
[9]   PHOTOCHEMICALLY GENERATED SILICON-CARBON DOUBLE-BONDED INTERMEDIATES .3. REACTION OF PARA-TOLYLPENTAMETHYLDISILANE WITH METHANOL AND METHANOL-D [J].
ISHIKAWA, M ;
FUCHIKAMI, T ;
KUMADA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 118 (02) :155-160
[10]   PHOTOCHEMICALLY GENERATED SILICON-CARBON DOUBLE-BONDED INTERMEDIATES .7. NEW ROUTE TO SILAETHENE DERIVATIVES FROM 1-ALKENYLDISILANES [J].
ISHIKAWA, M ;
FUCHIKAMI, T ;
KUMADA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 149 (01) :37-48