Secondary isotope effects in dioxirane epoxidations. Concerted or step-wise mechanism?

被引：11

作者：

Angelis, Y ^{[1
]}

Zhang, XJ ^{[1
]}

Orfanopoulos, M ^{[1
]}

机构：

[1] UNIV CRETE,DEPT CHEM,IRAKLION 71409,GREECE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 33期

关键词：

D O I：

10.1016/0040-4039(96)01256-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The inverse alpha- and beta-secondary isotope effects found for the epoxidation reaction of dimethyl dioxirane (DMD) with alkenes support a non polar concerted mechanism. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：5991 / 5994

页数：4

共 19 条

[1] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[2]

ADAM W, 1993, TOP CURR CHEM, V164, P45

[3] EPOXIDATION BY DIMETHYLDIOXIRANE - ELECTRONIC AND STERIC EFFECTS [J].

BAUMSTARK, AL ;

VASQUEZ, PC .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3437-3439

[4] EPOXIDATION OF ALKENES BY DIMETHYLDIOXIRANE - EVIDENCE FOR A SPIRO TRANSITION-STATE [J].

BAUMSTARK, AL ;

MCCLOSKEY, CJ .

TETRAHEDRON LETTERS, 1987, 28 (29) :3311-3314

[5] EPOXIDATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY DIMETHYLDIOXIRANE [J].

BAUMSTARK, AL ;

HARDEN, DB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7615-7618

[6] OXIDATION OF ALKYL AND ARYL IODIDES, PHENYLACETALDEHYDE AND ALKENES BY DIMETHYLDIOXIRANE - REACTION-PRODUCTS AND MECHANISM [J].

BRAVO, A ;

FONTANA, F ;

FRONZA, G ;

MINISCI, F ;

SERRI, A .

TETRAHEDRON LETTERS, 1995, 36 (38) :6945-6948

[7]

Carpender B.K., 1984, DETERMINATION ORGANI

[8] EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES [J].

CURCI, R ;

FIORENTINO, M ;

TROISI, L ;

EDWARDS, JO ;

PATER, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4758-4760

[9] FORMATION AND REACTIVITY OF DIOXIRANE INTERMEDIATES IN THE REACTION OF PEROXOANIONS WITH ORGANIC SUBSTRATES [J].

EDWARDS, JO ;

PATER, RH ;

CURCI, R ;

DIFURIA, F .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1979, 30 (01) :63-70

[10]

Melander L., 1980, Reaction Rates of Isotopic Molecules

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