DIOXIRANE OXIDATION OF (Z)-1-THIOAURONES, (E)-3-ARYLIDENE-1-THIOCHROMAN-4-ONES AND (E)-3-ARYLIDENE-1-THIOFLAVAN-4-ONES

被引：38

作者：

ADAM, W ^{[1
]}

GOLSCH, D ^{[1
]}

HADJIARAPOGLOU, L ^{[1
]}

LEVAI, A ^{[1
]}

NEMES, C ^{[1
]}

PATONAY, T ^{[1
]}

机构：

[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY

来源：

TETRAHEDRON | 1994年 / 50卷 / 46期

关键词：

D O I：

10.1016/S0040-4020(01)89320-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of the title compounds 1, 4 and 7 with dimethyldioxirane (DMD) afforded the corresponding sulfoxides 2, 5 and 8 and/or sulfones 3, 6 and 9 in good yields (Scheme 1 and 2). Excess dimethyldioxirane gave the sulfones chemoselectively without formation of the epoxides. The epoxidation of the sulfones 6a,b,d to the respective spiroepoxides 10a,b,d required the more reactive methyl(trifluoromethyl)dioxirane (TFD) as oxidant.

引用

页码：13113 / 13120

页数：8

共 31 条

[1] THIANTHRENE 5-OXIDE (SSO) AS A MECHANISTIC PROBE OF THE ELECTROPHILIC CHARACTER IN THE OXYGEN-TRANSFER BY DIOXIRANES [J].

ADAM, W ;

GOLSCH, D .

CHEMISCHE BERICHTE, 1994, 127 (06) :1111-1113

[2]

ADAM W, 1992, SYNTHESIS-STUTTGART, P436

[3] DIMETHYLDIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES, ACIDS AND ESTERS [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

NESTLER, B .

TETRAHEDRON LETTERS, 1990, 31 (03) :331-334

[4] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].

ADAM, W ;

CHAN, YY ;

CREMER, D ;

GAUSS, J ;

SCHEUTZOW, D ;

SCHINDLER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803

[5]

ADAM W, 1992, SYNTHESIS-STUTTGART, P49

[6] DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

SMERZ, A .

CHEMISCHE BERICHTE, 1991, 124 (01) :227-232

[7] THIANTHRENE 5-OXIDE AS A MECHANISTIC PROBE FOR ASSESSING THE ELECTRONIC CHARACTER OF OXYGEN-TRANSFER AGENTS [J].

ADAM, W ;

HAAS, W ;

LOHRAY, BB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6202-6208

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

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

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

[9]

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

[10] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

← 1 2 3 4 →