SYNTHESIS OF A CHIRAL MONOSUBSTITUTED DERIVATIVE OF BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE - REACTION OF THE CYCLIC SULFATE ESTER OF R,R-1,4-DIFLUOROBUTANE-2,3-DIOL WITH 2-THIOXO-1,3-DITHIOLE-4,5-DITHIOLATE

被引:38
作者
OZTURK, T [1 ]
RICE, CR [1 ]
WALLIS, JD [1 ]
机构
[1] UNIV KENT,CHEM LAB,MAT RES CTR,CANTERBURY CT2 7NH,KENT,ENGLAND
关键词
D O I
10.1039/jm9950501553
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
2-Thioxo-1,3-dithiole-4 5-dithiolate reacts stereospecifically with the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol by two nucleophilic attacks, ring opening of the cyclic sulfate ester at carbon and displacement of the nearer fluorine atom, to form a derivative of the 1,3-dithiolo[4,5-b]-1,4-dithiin ring system. This product is converted in two steps into an analogue of bis(ethylenedithio)tetrathiafulvalene with a 2-fluoro-1-hydroxyethyl side-chain, a new substrate for the preparation of electroactive materials.
引用
收藏
页码:1553 / 1556
页数:4
相关论文
共 16 条
[1]   TOXIC FLUORINE COMPOUNDS CONTAINING THE C-F LINK .11. LABILITY OF THE FLUORINE ATOM IN 2-FLUOROETHANOL [J].
BRONNERT, DLE ;
SAUNDERS, BC .
TETRAHEDRON, 1960, 10 (3-4) :160-163
[2]  
CHAMBERS RJ, 1973, FLUORINE ORGANIC CHE, P100
[3]   Reactivity and influence of fluorine in aliphatic compounds [J].
Henne, AL ;
Midgley, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :882-884
[4]  
IQBAL Z, 1991, SCIENCE, V254, P8263
[5]   A NEW AMBIENT-PRESSURE ORGANIC SUPERCONDUCTOR, KAPPA-(ET)2CU[N(CN)2]BR, WITH THE HIGHEST TRANSITION-TEMPERATURE YET OBSERVED (INDUCTIVE ONSET TC = 11.6 K, RESISTIVE ONSET = 12.5 K) [J].
KINI, AM ;
GEISER, U ;
WANG, HH ;
CARLSON, KD ;
WILLIAMS, JM ;
KWOK, WK ;
VANDERVOORT, KG ;
THOMPSON, JE ;
STUPKA, DL ;
JUNG, D ;
WHANGBO, MH .
INORGANIC CHEMISTRY, 1990, 29 (14) :2555-2557
[6]   ONE POT SYNTHESIS OF HOMOCHIRAL AZIRIDINES AND AMINOALCOHOLS FROM HOMOCHIRAL 1,2-CYCLIC SULFATES [J].
LOHRAY, BB ;
GAO, Y ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1989, 30 (20) :2623-2626
[7]   FUNCTIONALIZED TETRATHIAFULVALENE (TTF) SYSTEMS DERIVED FROM 4,5-(PROPYLENEDITHIO)-1,3-DITHIOLE UNITS [J].
MARSHALLSAY, GJ ;
BRYCE, MR ;
COOKE, G ;
JORGENSEN, T ;
BECHER, J ;
REYNOLDS, CD ;
WOOD, S .
TETRAHEDRON, 1993, 49 (31) :6849-6862
[8]   TOXIC FLUORINE COMPOUNDS CONTAINING THE C-F LINK .10. RUPTURE OF THE C-F LINK BY ALKALI AND OTHER REAGENTS [J].
MIROSEVICSORGO, P ;
SAUNDERS, BC .
TETRAHEDRON, 1959, 5 (01) :38-43
[9]   STEREOSPECIFIC CONVERSION OF CHIRAL 1,2-CYCLIC SULFATES TO CHIRAL IMIDAZOLINES [J].
OI, R ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1991, 32 (08) :999-1002
[10]   SHORT INTERMOLECULAR S...S CONTACTS IN A REACTION-PRODUCT FROM THE CYCLIC SULFATE ESTER OF DIMETHYL L-TARTRATE AND 2-THIOXO-1,3-DITHIOLE-4,5-DITHIOLATE [J].
OZTURK, T ;
POVEY, DC ;
WALLIS, JD .
TETRAHEDRON, 1994, 50 (38) :11205-11212