Oxidation of 2-(4-chlorobenzoyl)-thiophene into 1-oxide Diels-Alder dimers, sesquioxide and a sulfone-water adduct.

被引：7

作者：

Ho, MT ^{[1
]}

Treiber, A ^{[1
]}

Dansette, PM ^{[1
]}

机构：

[1] Univ Paris 05, Chim & Biochim Pharmacol & Toxicol Lab, CNRS, URA 400, F-75270 Paris 06, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 28期

关键词：

thiophene; oxidation; peracid; dioxirane;

D O I：

10.1016/S0040-4039(98)01004-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of 4-chlorophenyl, thien-2-yl-methanone 1 with 0.2 eq H2O2 in TFA gave the 1-oxide Diels-Alder dimer 3a. Use of an 1-5 eq H2O2 afforded the sesquioxide 4 (4,7 di [4-chlorobenzoyl]-3,10-dithiatricyclo [5.2.1.0(2,6)] deca-4,8-diene 3,3,10-trioxide). Oxidation of 1 with mCPBA in CH2Cl2-excess BF3-etherate gave 3a (4,7-di [4-chlorobenzoyl]-3,10-dithiatricyclo [5.2.1.0(2,6)] deca-4,8-diene 3,10-dioxide) in acceptable yield and the minor isomer 3b in low yield. Oxidation of 1 with 6 eq dimethyldioxirane in acetone gave 3-hydroxy 2,3-dihydrothiophene 1,1-dioxide 6, a 1,1-dioxide-water adduct. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5049 / 5052

页数：4

共 3 条

[1] MOLECULAR AND CRYSTAL STRUCTURE OF P2O4C12H18, 1,8-DIETHOXY-3A,4,7,7A-TETRAHYDRO-4,7-PHOSPHINIDENE-PHOSPHINDIOLE 1,8-DIOXIDE . A DIELS-ALDER DIMER OF 1-ETHOXYPHOSPHOLE 1-OXIDE
CHIU, YYH
LIPSCOMB, WN
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (15) : 4150 - &
[2] 1,7,8,9-TETRAMETHYL-2,3,5,6-TETRAKIS(TRIFLUOROMETHYL)-4-THIA-10-OXATETRACYCLO[5,2,1,02,6,03,5]DEC-8-ENE - DIELS-ALDER ADDUCT FROM A DEWAR-TYPE THIOPHENE DERIVATIVE AND A FURAN DERIVATIVE
KIKUTANI, N
IITAKA, Y
KOBAYASHI, Y
KUMADAKI, I
OHSAWA, A
SEKINE, Y
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 1975, 31 (MAY15): : 1478 - 1480
[3] GREEN APPROACH USING WATER MEDIATED DIELS-ALDER REACTION FOR THE SYNTHESIS OF SOME 2-(4-BROMO-1-NAPHTHYL)-3-(ARYL) BICYCLO [2.2.1] HEPT-5-ENE METHANONES AND EVALUATION OF THEIR ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES
Thirunarayanan, Ganesamoorthy
MACEDONIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING, 2017, 36 (01) : 1 - 14

← 1 →