DEHYDROSILYLATION VERSUS ALPHA-COUPLING IN THE ELECTRON-TRANSFER OF ENOL SILYL ETHERS TO QUINONES - STRONG SOLVENT EFFECT ON PHOTOGENERATED ION-PAIRS

被引:24
作者
BOCKMAN, TM
PERRIER, S
KOCHI, JK
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 04期
关键词
D O I
10.1039/p29930000595
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Time-resolved (picosecond) spectroscopy identifies the critical role of solvent polarity in modulating the ion-pair dynamics of the reactive intermediate [CTE.+, CA.-] from the photoinduced electron transfer of cyclohexanone enol trimethylsilyl ether (CTE) and chloranil (CA) to yield selectively the dehydrosilylated enone 1 in dichloromethane but the oxidative adduct 2 in acetonitrile.
引用
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页码:595 / 597
页数:3
相关论文
共 33 条
[1]   OPTICAL SPECTRUM OF CHLORANIL RADICAL ANION [J].
ANDRE, JJ ;
WEILL, G .
MOLECULAR PHYSICS, 1968, 15 (01) :97-&
[2]   ORGANIC PHOTOCHEMISTRY .V. ILLUMINATION OF SOME QUINONES IN PRESENCE OF CONJUGATED DIENES AND OTHER OLEFINIC SYSTEMS [J].
BARLTROP, JA ;
HESP, B .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (17) :1625-&
[3]   2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE (DDQ) OXIDATION OF SILYL ENOL ETHERS TO ENONES VIA DDQ-SUBSTRATE ADDUCTS [J].
BHATTACHARYA, A ;
DIMICHELE, LM ;
DOLLING, UH ;
GRABOWSKI, EJJ ;
GRENDA, VJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6118-6120
[4]  
BOCKMAN TM, UNPUB
[5]  
BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P1
[6]   A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES [J].
CAZEAU, P ;
DUBOUDIN, F ;
MOULINES, F ;
BABOT, O ;
DUNOGUES, J .
TETRAHEDRON, 1987, 43 (09) :2075-2088
[7]   DIRECT AND REGIOCONTROLLED SYNTHESIS OF ALPHA-PHENYL KETONES FROM SILYL ENOL ETHERS AND DIPHENYLIODONIUM FLUORIDE [J].
CHEN, KC ;
KOSER, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5764-5767
[8]   NUCLEOPHILE-ASSISTED CLEAVAGE OF SILANE CATION RADICALS [J].
DINNOCENZO, JP ;
FARID, S ;
GOODMAN, JL ;
GOULD, IR ;
TODD, WP ;
MATTES, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8973-8975
[9]   ELECTRON-TRANSFER INDUCED DESILYLATION OF TRIMETHYLSILYL ENOL ETHERS [J].
GASSMAN, PG ;
BOTTORFF, KJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1097-1100
[10]  
GSCHWIND R, 1979, HELV CHIM ACTA, V62, P944