CHALCOGENATION OF TETRATHIAFULVALENE (TTF) - SYNTHESIS OF ALKYLTHIO-TTF AND ALKYLSELENO-TTF DERIVATIVES AND X-RAY CRYSTAL-STRUCTURE OF ETHYLENEDISELENO-TTF (EDS-TTF)

被引：25

作者：

MOORE, AJ

BRYCE, MR

COOKE, G

MARSHALLSAY, GJ

SKABARA, PJ

BATSANOV, AS

HOWARD, JAK

DALEY, STAK

机构：

[1] UNIV DURHAM,DEPT CHEM,DURHAM DH1 3LE,ENGLAND

[2] ICI FCMO,HUDDERSFIELD HD2 1FF,YORKS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 13期

关键词：

D O I：

10.1039/p19930001403

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of mono-lithiated tetrathiafulvalene (TTF) with elemental sulfur or elemental selenium at -78-degrees-C yields the transient species TTF-S- Li+ and TTF-Se- Li+, respectively, which have been trapped with a range of alkyl halides to yield new alkylthio- and alkylseleno-TTF derivatives. Reaction of the TTF-thiolate anion with 2-bromoethanol yields 4-(2-hydroxyethylthio)tetrathiafulvalene which is a particularly versatile building block for the synthesis of a range of new mono-functionalised TTF derivatives containing ether, ester, acrylate, urethane and vinylthio groups in the side chain. One-pot syntheses of ethylenedithio-TTF (EDT-TTF) and ethylenediseleno-TTF (EDS-TTF) from TTF are reported. The structure of EDS-TTF has been determined by single crystal X-ray analysis which reveals dimers with molecular planes orthogonal to each other.

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页码：1403 / 1410

页数：8

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