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

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