DIMETHYLDIOXIRANE EPOXIDATION OF ALKENES BEARING 2 ELECTRON DONATING SUBSTITUENTS

被引：22

作者：

ADAM, W

HADJIARAPOGLOU, L

WANG, XH

机构：

[1] Institute of Organic Chemistry, University of Würzburg, W-8700 Würzburg, Am Hubland

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(00)79649-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various enol-type alkenes, such as 2,3-dimethylbenzodioxin (1), O-tetrabenzyl glycal (3), 1,2-bis(trimethylsilyloxy)cycloalkenes (9) were transformed in excellent yields to their labile epoxides by dimethyldioxirane (as acetone solution); the silyl ketene acetal 5 and 2-methyl-3-trimethylsilyloxybenzo[b]furan (7) gave the corresponding epoxide rearrangement products.

引用

页码：1295 / 1298

页数：4

共 23 条

[1] DIMETHYLDIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES, ACIDS AND ESTERS
ADAM, W
HADJIARAPOGLOU, L
NESTLER, B
[J]. TETRAHEDRON LETTERS, 1990, 31 (03) : 331 - 334
[2] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS
ADAM, W
CHAN, YY
CREMER, D
GAUSS, J
SCHEUTZOW, D
SCHINDLER, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2800 - 2803
[3] DIMETHYLDIOXIRANE EPOXIDATION OF ENOL PHOSPHATES
ADAM, W
HADJIARAPOGLOU, L
KLICIC, J
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6517 - 6520
[4] DIMETHYLDIOXIRANE EPOXIDATION OF BETA-OXO ENOL ETHERS
ADAM, W
HADJIARAPOGLOU, L
[J]. CHEMISCHE BERICHTE, 1990, 123 (10) : 2077 - 2079
[5] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[6] EPOXIDATION OF GAMMA-METHYLENE-GAMMA-BUTYROLACTONES BY DIMETHYLDIOXIRANE
ADAM, W
HADJIARAPOGLOU, L
JAGER, V
SEIDEL, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (32) : 4223 - 4226
[7] ADAM W, UNPUB TETRAHEDRON LE
[8] ADAM W, 1989, TETRAHEDRON LETT, V30, P6597
[9] ADAM W, 1991, IN PRESS CHEM BER, V124
[10] ADAM W, 1991, IN PRESS ANGEW CHEM, V103

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