Synthesis of 4,6-dimethyl-tetrahydro- and hexahydro-dibenzothiophene

被引：8

作者：

Sun, Yinyong ^{[1
]}

Wang, Huamin ^{[1
]}

Prins, Roel ^{[1
]}

机构：

[1] ETH, Inst Chem & Bioengn, CH-8093 Zurich, Switzerland

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 13期

关键词：

conjugate addition; 2-bromo-3-methylcyclohexanone; Tilak annulation; 4,6-dimethyldibenzothiophene;

D O I：

10.1016/j.tetlet.2008.02.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Bromo-3-methylcyclohexanone was synthesized by conjugate addition of trimethylaluminium to 2-bromo-2-cyclohexen-1-one with copper bromide as catalyst, coupled with 2-methylthiophenol and annulated with the aid of polyphosphoric acid to 4,6-dimethyl-1,2,3,4-tetrahydrodibenzothiophene. The latter was hydrogenated to 4,6-dimethyl-1,2,3,4,4a,9b-hexahydrodibenzothiophene, another intermediate in the hydrodesulfurization of 4,6-dimethyldibenzothiophene, by zinc and trifluoroacetic acid, and dehydrogenated to 4,6-dimethyldibenzothiophene. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2063 / 2065

页数：3

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