Accelerated electrocyclic ring-opening of benzocyclobutenes under the influence of β-silicon atom

被引:24
作者
Matsuya, Y [1 ]
Ohsawa, N [1 ]
Nemoto, H [1 ]
机构
[1] Toyama Univ, Fac Pharmaceut Sci, Toyama 9300194, Japan
关键词
D O I
10.1021/ja055505+
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A significant acceleration effect of a β-silicon atom was observed on the electrocyclic ring-opening reaction of benzocyclobutene derivatives to form o-quinodimethanes. This acceleration effect could be attributed to an electronic σ-donating nature of the C(α)-Si(β) bond, associated with α-anion driven pericyclic reactions. Copyright © 2006 American Chemical Society.
引用
收藏
页码:412 / 413
页数:2
相关论文
共 25 条
[1]   DIELS-ALDER REACTIONS OF ALPHA-OXY-ORTHO-XYLYLENES [J].
CHOY, W ;
YANG, HL .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5796-5798
[2]   Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].
Dolbier, WR ;
Koroniak, H ;
Houk, KN ;
Sheu, CM .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (10) :471-477
[3]   [3,3]SIGMATROPIC REARRANGEMENTS OF 1,5-DIENE ALKOXIDES - POWERFUL ACCELERATING EFFECTS OF ALKOXIDE SUBSTITUENT [J].
EVANS, DA ;
GOLOB, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4765-4766
[4]  
HUISGEN R, 1964, TETRAHEDRON LETT, V5, P3381
[5]   Geminal bond participation in the electrocyclic reactions: Torquoselectivities of silyl and trimethylsilyl derivatives of cyclobutene, iminocyclobutene, and cyclobutenone [J].
Ikeda, H ;
Kato, T ;
Inagaki, S .
CHEMISTRY LETTERS, 2001, (03) :270-271
[6]   TORQUOSELECTIVITY IN THE ELECTROCYCLIC CONVERSION OF BENZOCYCLOBUTENES TO ORTHO-XYLYLENES [J].
JEFFORD, CW ;
BERNARDINELLI, G ;
WANG, Y ;
SPELLMEYER, DC ;
BUDA, A ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1157-1165
[7]   STUDIES ON SYNTHESES OF HETEROCYCLIC-COMPOUNDS .675. FACILE REGIOSPECIFIC AND STEREOCONTROLLED SYNTHESIS OF A DITERPENE ALKALOID INTERMEDIATE FROM BENZOCYCLOBUTENES [J].
KAMETANI, T ;
KATO, Y ;
HONDA, T ;
FUKUMOTO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (25) :8185-8190
[8]   CONCERTED RING-OPENING REACTION OF CYCLOBUTENES - THE EXTRAORDINARY ACCELERATING EFFECTS OF ARYLSULFOXY AND SULFONYL CARBANION SUBSTITUENTS [J].
KAMETANI, T ;
TSUBUKI, M ;
NEMOTO, H ;
SUZUKI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (05) :1256-1258
[9]   COMPETITIVE REACTIONS BETWEEN SIGMATROPIC REACTION AND CYCLOADDITION AFFECTED BY GEOMETRY OF ORTHO-QUINODIMETHANES [J].
KAMETANI, T ;
TSUBUKI, M ;
SHIRATORI, Y ;
KATO, Y ;
NEMOTO, H ;
IHARA, M ;
FUKUMOTO, K ;
SATOH, F ;
INOUE, H .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (16) :2672-2676
[10]   STEREOSELECTIVE SUBSTITUENT EFFECTS ON CONROTATORY ELECTROCYCLIC REACTIONS OF CYCLOBUTENES [J].
KIRMSE, W ;
RONDAN, NG ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) :7989-7991