Acetolysis of styryl and 1-decenyl iodonium salts. Occurrence of two-step mechanism via vinylenephenonium ion and one-step inversion mechanism

被引:54
作者
Okuyama, T [1 ]
Ochiai, M [1 ]
机构
[1] UNIV TOKUSHIMA,FAC PHARMACEUT SCI,TOKUSHIMA 770,JAPAN
关键词
D O I
10.1021/ja9705607
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[No abstract available]
引用
收藏
页码:4785 / 4786
页数:2
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共 9 条
[1]   IS S(N)2 SUBSTITUTION WITH INVERSION OF CONFIGURATION AT VINYLIC CARBON FEASIBLE [J].
GLUKHOVTSEV, MN ;
PROSS, A ;
RADOM, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5961-5962
[2]   AN AUTHENTIC CASE OF INPLANE NUCLEOPHILIC VINYLIC SUBSTITUTION - THE ANIONOTROPIC REARRANGEMENT OF DI-TERT-BUTYLTHIIRENIUM IONS INTO THIETIUM IONS [J].
LUCCHINI, V ;
MODENA, G ;
PASQUATO, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4527-4531
[3]   S(N)2 AND AD(N)-E MECHANISMS IN BIMOLECULAR NUCLEOPHILIC SUBSTITUTIONS AT VINYL CARBON - THE RELEVANCE OF THE LUMO SYMMETRY OF THE ELECTROPHILE [J].
LUCCHINI, V ;
MODENA, G ;
PASQUATO, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (08) :2297-2300
[4]   INVERSION OF CONFIGURATION IN NUCLEOPHILIC VINYLIC SUBSTITUTIONS OF (E)-BETA-ALKYLVINYLIODONIUM TETRAFLUOROBORATES WITH HALIDES [J].
OCHIAI, M ;
OSHIMA, K ;
MASAKI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7059-7061
[5]   REACTIONS OF VINYLSILANES WITH LEWIS ACID-ACTIVATED IODOSYLBENZENE - STEREOSPECIFIC SYNTHESES OF VINYLIODONIUM TETRAFLUOROBORATES AND THEIR REACTIONS AS HIGHLY ACTIVATED VINYL HALIDES [J].
OCHIAI, M ;
SUMI, K ;
TAKAOKA, Y ;
KUNISHIMA, M ;
NAGAO, Y ;
SHIRO, M ;
FUJITA, E .
TETRAHEDRON, 1988, 44 (13) :4095-4112
[6]   SOLVOLYSIS OF CYCLOHEXENYLIODONIUM SALT, A NEW PRECURSOR FOR THE VINYL CATION - REMARKABLE NUCLEOFUGALITY OF THE PHENYLIODONIO GROUP AND EVIDENCE FOR INTERNAL RETURN FROM AN INTIMATE ION-MOLECULE PAIR [J].
OKUYAMA, T ;
TAKINO, T ;
SUEDA, T ;
OCHIAI, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3360-3367
[7]   VINYLIC SUBSTITUTION OF 1,2-DIBROMO-1,2-DIFLUOROETHYLENE AND TRIBROMOFLUOROETHYLENE - AN INTRAMOLECULAR KAPPA(BR)/KAPPA(F) ELEMENT EFFECT AND APPARENT INVERSION OF CONFIGURATION IN SNV REACTIONS [J].
SHAINYAN, BA ;
RAPPOPORT, Z .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3421-3428
[8]   VINYL TRIFLATE CHEMISTRY - UNSATURATED CATIONS AND CARBENES [J].
STANG, PJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (03) :107-114
[9]   MECHANISM OF REACTION OF CIS-3-PHENYL-2-BUTEN-2-YL AND TRANS-3-PHENYL-2-BUTEN-2-YL TRIFLATES - EVIDENCE FOR VINYLIDENE PHENONIUM IONS [J].
STANG, PJ ;
DUEBER, TE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) :2602-2610