Efficient synthesis of brominated tetrathiafulvalene (TTF) derivatives:: solid-state structure and electrochemical behaviour

被引：8
作者：
Alberola, Antonio [1 ]
Collis, Rebecca J. [1 ]
Garcia, Felipe [1 ]
Howard, Ruth E. [1 ]
机构：
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
来源：
TETRAHEDRON | 2006年 / 62卷 / 34期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/j.tet.2006.06.006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis is reported for 4,5-dibromo-[1,3]dithiole-2-thione (1) and 4-bromo-1,3-dithiole-2-thione (7) by bromination of lithiated vinylene trithiocarbonate. Compound 1 acts as a convenient precursor to a number of asymmetric electron donors. This is exemplified by the formation of 4,5-dibromo-4',5'-bis(2'-cyanoethylsulfanyl)TTF (3) by cross-coupling methodology and subsequent conversion into 4,5-dibromo-4',5'-ethylenedithioTTF (4) by reaction with caesium hydroxide and 1,2-dibromoethane. The new donor 4,5-dibromo4',5'-ethylenedithiodiselenadithiafulvalene (5) was prepared by cross-coupling of 1 and 4,5-ethylenedithio-1,3-diselenol-2-one (6). The X-ray structures of 3 and 5 are reported. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：8152 / 8157
页数：6
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