Chemistry of thioacylsilanes .11. Cyclic and open chain alpha-silyl vinyl sulfides as precursors of thioannulated cyclopentenones and thiofunctionalized enones

被引：11

作者：

Bonini, BF

Franchini, MC

Fochi, M

Mazzanti, G

Ricci, A

机构：

[1] Dipartmento Chim. Organ. A. Mangini, Facoltà di Chim. Industriale, 40136 Bologna

来源：

TETRAHEDRON | 1997年 / 53卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(97)00462-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic and open chain a-silyl vinyl sulfides, obtained from thioacylsilanes, react with acid chlorides in the presence of Lewis acid to give thioannulated cyclopentenones and thiofunctionalized enones. The effect of the substituents at silicon on these reactions has been investigated. (C) 1997 Elsevier Science Ltd.

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收藏

页码：7897 / 7910

页数：14

相关论文

共 21 条

[1] ELECTROPHILIC REACTIONS OF "1-PHENYLTHIO-1-TRIMETHYISILYLETHENE [J].

AGER, DJ .

TETRAHEDRON LETTERS, 1982, 23 (18) :1945-1946

[2] Chemistry of silyl thioketones .10. Synthesis and reactivity of alpha-silyl vinyl sulfides [J].

Bonini, BF ;

ComesFranchini, M ;

Fochi, M ;

Mazzanti, G ;

Peri, F ;

Ricci, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (23) :2803-2809

[3] Chemistry of silyl thioketones .9. A new selective synthesis of 1-silyl-1-enethiols and of 2-silyl-thiacycloalk-2-enes of common to large ring size. [J].

Bonini, BF ;

ComesFranchini, M ;

Fochi, M ;

Mazzanti, G ;

Ricci, A .

TETRAHEDRON, 1996, 52 (13) :4803-4816

[4]

CASADEI MA, 1981, J ORG CHEM, V46, P3177

[5]

Colvin E. W., 1981, SILICON ORGANIC SYNT, P125

[6]

Colvin E. W, 1981, SILICON ORGANIC SYNT, P15

[7] SILICON IN SYNTHESIS .8. VINYLTRIMETHYLSILANE, A CONVENIENT ETHYLENE EQUIVALENT FOR THE SYNTHESIS OF VINYL ARYL SULFIDES, VINYL ARYL SULFOXIDES, THIOSILYLKETENE ACETALS, AND FUSED CYCLOPENTENONES [J].

COOKE, F ;

MOERCK, R ;

SCHWINDEMAN, J ;

MAGNUS, P .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1046-1053

[8] SILICON-DIRECTED NAZAROV CYCLIZATION [J].

DENMARK, SE ;

JONES, TK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2642-2645

[9] SILICON-DIRECTED NAZAROV CYCLIZATIONS .4. FURTHER-STUDIES IN STEREOCHEMICAL CONTROL [J].

DENMARK, SE ;

HABERMAS, KL ;

HITE, GA ;

JONES, TK .

TETRAHEDRON, 1986, 42 (11) :2821-2829

[10] THE PHENYLDIMETHYLSILYL GROUP AS A MASKED HYDROXY GROUP [J].

FLEMING, I ;

HENNING, R ;

PARKER, DC ;

PLAUT, HE ;

SANDERSON, PEJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (04) :317-337