AN EXTREMELY EFFICIENT SYNTHESIS OF THIOPHENE 1,1-DIOXIDES - OXIDATION OF THIOPHENE DERIVATIVES WITH DIMETHYLDIOXIRANE

被引：41

作者：

MIYAHARA, Y

INAZU, T

机构：

[1] Department of Chemistry, Faculty of Science, Kyushu University 33 Hakozaki, Higashi-ku, Fukuoka

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)98003-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dimethyldioxirane was found to oxidize electron-rich thiophene derivatives, including sterically hindered thiophenophanes, to the corresponding thiophene 1,1-dioxides in excellent yields. Electronwithdrawing groups on a thiophene ring substantially retarded the oxidation, but dimethyldioxitane remained superior to other reagents. © 1990.

引用

页码：5955 / 5958

页数：4

共 32 条

[11] KARLSSON JO, 1982, ACTA CHEM SCAND B, V36, P341, DOI 10.3891/acta.chem.scand.36b-0341
[12] NEW EPOXIDATION WITH M-CHLOROPERBENZOIC ACID AT ELEVATED-TEMPERATURES
KISHI, Y
SUGIURA, S
TANINO, H
GOTO, T
ARATANI, M
KAKOI, H
INOUE, S
FUKUYAMA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (02) : 64 - &
[13] INTRAMOLECULAR 2H GROUP-TRANSFER (DYOTROPIC REARRANGEMENTS) IN ALICYCLIC AND HETEROCYCLIC BRIDGED-RING SYSTEMS
MACKENZIE, K
PROCTOR, G
WOODNUTT, DJ
[J]. TETRAHEDRON, 1987, 43 (24) : 5981 - 5993
[14] MELLES JL, 1953, RECL TRAV CHIM PAY B, V72, P314
[15] SYNTHESIS AND CONFORMATIONAL PROPERTIES OF 5,7-DISUBSTITUTED [3.3]METACYCLO(2,5)THIOPHENOPHANE-1,12-DIONES
MIYAHARA, Y
INAZU, T
YOSHINO, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (04) : 415 - 418
[16] NEW APPROACH TO SYNTHESIS OF THIOPHENOPHANES - SYNTHESIS OF [N.1.1] PARACYCLO (2,5) THIOPHENOPARACYCLOPHANES
MIYAHARA, Y
INAZU, T
YOSHINO, T
[J]. CHEMISTRY LETTERS, 1978, (06) : 563 - 566
[17] SYNTHESIS AND PROPERTIES OF [3.3] (2,5) FURANO (2,5) THIOPHENOPHANE AND [3.3] (2,5) THIOPHENOPHANE
MIYAHARA, Y
INAZU, T
YOSHINO, T
[J]. CHEMISTRY LETTERS, 1980, (04) : 397 - 400
[18] SYNTHESIS AND CONFORMATIONAL PROPERTIES OF [N.1.1]PARACYCLO(2,5)THIOPHENOPARACYCLOPHANES
MIYAHARA, Y
INAZU, T
YOSHINO, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (07) : 1177 - 1182
[19] EFFICIENT GUAIAZULENE AND CHAMAZULENE SYNTHESES INVOLVING [6+4] CYCLOADDITIONS
MUKHERJEE, D
DUNN, LC
HOUK, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) : 251 - 252
[20] CHEMISTRY OF DIOXIRANES .6. ELECTRONIC EFFECTS IN THE OXIDATION OF SULFIDES AND SULFOXIDES BY DIMETHYLDIOXIRANE
MURRAY, RW
JEYARAMAN, R
PILLAY, MK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) : 746 - 748

← 1 2 3 4 →