Access to 3,4-furan dithiolate:: towards 3,4-dialkylsulfanylfurans and their Diels-Alder adducts with acrylonitrile

被引：6

作者：

Frère, P

Gallego-Planas, N

Blanchard, P

Mabon, G

Rondeau, D

机构：

[1] Univ Angers, CNRS UMR 6501, F-49045 Angers, France

[2] Univ Angers, Serv Commun Anal Spect, F-49045 Angers, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 10期

关键词：

furan; 3,4-disubstituted furans; Diels-Alder reaction;

D O I：

10.1016/S0040-4039(02)00126-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The convenient synthesis of symmetrical and unsymmetrical 3,4-dialkylsulfanylfurans from 3,4-furandithiolate is described. The reactivity of the furan cycle as a diene in Diels-Alder reactions with acrylonitrile is discussed in relation to the presence of one or two thiolato substituents. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：1825 / 1828

页数：4

相关论文

共 16 条

[1] An analysis of substituent effects on 1H and 13C NMR parameters of substituted furans.: Linear free energy relationships and PM3 semiempirical calculations [J].

Alvarez-Ibarra, C ;

Quiroga-Feijoo, ML ;

Toledano, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (03) :679-689

[2] Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran [J].

AlvarezIbarra, C ;

Quiroga, ML ;

Toledano, E .

TETRAHEDRON, 1996, 52 (11) :4065-4078

[3] CESIUM TETRATHIAFULVALENE-THIOLATES - KEY SYNTHETIC INTERMEDIATES [J].

BECHER, J ;

LAU, J ;

LERICHE, P ;

MORK, P ;

SVENSTRUP, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (23) :2715-2716

[4] Difuryl polyenes as precursors of highly conducting electrogenerated conjugated polymers [J].

BenahmedGasmi, A ;

Frere, P ;

Roncali, J .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1996, 406 (1-2) :231-234

[5]

Bird C.W., 1984, COMPREHENSIVE HETERO, V4

[6]

Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01

[7] POLYFURAN - A NEW SYNTHETIC APPROACH AND ELECTRONIC-PROPERTIES [J].

GLENIS, S ;

BENZ, M ;

LEGOFF, E ;

SCHINDLER, JL ;

KANNEWURF, CR ;

KANATZIDIS, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12519-12525

[8] POLYFURAN - ELECTROSYNTHESIS AND ELECTROCHEMICAL-BEHAVIOR [J].

GONZALEZTEJERA, MJ ;

CARRILLO, I ;

HERNANDEZFUENTES, I .

SYNTHETIC METALS, 1995, 73 (02) :135-140

[9] VERSATILITY OF THE REACTIVITY OF DICARBALDEHYDE ACETYLENE AND ALPHA-ACETYLENIC ALDEHYDES CONCERNING CYCLIC AND HETEROCYCLIC CONJUGATED DIENES IN ACIDIC MEDIA [J].

GORGUES, A ;

SIMON, A ;

LECOQ, A ;

HERCOUET, A ;

CORRE, F .

TETRAHEDRON, 1986, 42 (01) :351-370

[10] ACETYLENEDICARBALDEHYDE - ISOLATION AND EXCLUSIVE DIENOPHILIC ACTIVITY UNDER NEUTRAL CONDITIONS [J].

GORGUES, A ;

STEPHAN, D ;

BELYASMINE, A ;

KHANOUS, A ;

LECOQ, A .

TETRAHEDRON, 1990, 46 (08) :2817-2826