PYRAZINE-FUSED BIS(TETRATHIAFULVALENES)

被引:16
作者
LAHLIL, K
MORADPOUR, A
MERIENNE, C
BOWLAS, C
机构
[1] UNIV PARIS 11,PHYS SOLIDES LAB,CNRS,UA 2,F-91405 ORSAY,FRANCE
[2] UNIV PARIS 11,CHIM & PHYS CHIM MILIEUX STRUCT LAB,CNRS,UA 1384,F-91405 ORSAY,FRANCE
[3] CNRS,CHIM COORDINAT LAB,F-31077 TOULOUSE,FRANCE
关键词
D O I
10.1021/jo00105a018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The TTF-like bidentate sulfur nucleophiles 13a,b have been prepared from the corresponding 4,5-dialkyl-1,3-dithiole S-oxides 11a,b, obtained by the oxidation of the parent 1,3-dithioles 10a,b. The aromatic nucleophilic substitutions of tetrachloropyrazine by these nucleophiles 13a,b yield, in a single step, the unsymmetrically substituted pyrazino-TTF 8 or the pyrazine-fused bis-TTF 9a,b depending on the stoeichiometries of the reactions. The electrochemical properties of these new donors, obtained by cyclic voltammetry, are also reported.
引用
收藏
页码:8030 / 8033
页数:4
相关论文
共 29 条
[1]   POLYFLUOROHETEROCYCLIC COMPOUNDS .17. PREPARATION AND NUCLEOPHILIC SUBSTITUTION OF TETRAFLUOROPYRAZINE AND ORIENTATIONAL EFFECT OF SUBSTITUENTS IN POLYSUBSTITUTION [J].
ALLISON, CG ;
CHAMBERS, RD ;
MACBRIDE, JA ;
MUSGRAVE, WK .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (08) :1023-&
[2]   BIS(TETRATHIAFULVALENES) AND TRIS(TETRATHIAFULVALENES) (TTFS) DERIVED FROM REACTIONS OF THE TTF-THIOLATE ANION [J].
BRYCE, MR ;
MARSHALLSAY, GJ ;
MOORE, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) :4859-4862
[3]   FRAGMENTATION OF ORGANIC-ANIONS INDUCED BY EXOTHERMIC ADDITION-REACTIONS [J].
DEPUY, CH .
ORGANIC MASS SPECTROMETRY, 1985, 20 (09) :556-559
[4]   THE C3H5-ISOMERS - EXPERIMENTAL AND THEORETICAL-STUDIES OF TAUTOMERIC PROPENYL IONS AND THE CYCLOPROPYL ANION IN THE GAS-PHASE [J].
FROELICHER, SW ;
FREISER, BS ;
SQUIRES, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :2853-2862
[5]   REGIOCHEMICAL EFFECTS ASSOCIATED WITH NUCLEOPHILIC AROMATIC SUBSTITUTIONS BY BIDENTATE SULFUR NUCLEOPHILES [J].
GIMBERT, Y ;
MORADPOUR, A ;
MERIENNE, C .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5347-5350
[6]   REACTIONS OF 2-LITHIO-1,3-BENZODITHIOLE WITH CARBON-DISULFIDE - FORTH AND BACK PROCESSES [J].
GIMBERT, Y ;
MORADPOUR, A ;
BITTNER, S ;
JORDIS, U .
TETRAHEDRON LETTERS, 1989, 30 (07) :819-822
[7]  
GROBEL BT, 1977, SYNTHESIS-STUTTGART, P357
[8]  
GRUNWELL JR, 1971, INT J SULFUR CHEM, V1, P60
[9]   NEW EXTENDED PI-ELECTRON DONORS - TETRATHIAFULVALENE SYSTEMS WITH HETEROCYCLIC SPACER GROUPS [J].
HANSEN, TK ;
LAKSHMIKANTHAM, MV ;
CAVA, MP ;
NIZIURSKIMANN, RE ;
JENSEN, F ;
BECHER, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5035-5039
[10]  
JORGENSEN M, 1991, J ORG CHEM, V56, P5684