First synthesis and structure of sulfur-containing heterocycles fused to ferrocene

被引:12
作者
Nagahora, N
Ogawa, S [1 ]
Kawai, Y
Sato, R
机构
[1] Iwate Univ, Fac Engn, Dept Chem Engn, Morioka, Iwate 0208551, Japan
[2] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan
关键词
sulfur heterocycles; ferrocenes; X-ray crystal structures; electrochemistry;
D O I
10.1016/S0040-4039(02)01172-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of a stable pentathiepin fused to a single cyclopentadienyl ring of ferrocene was performed by treatment of the corresponding dithiastannole as a synthetic equivalent of unstable ferrocene 1,2-dithiol with a sulfur source. On the other hand, deprotection of the dithinstannole gave a novel tetrathiocin comprised of two ferrocene units. The single-crystal X-ray diffraction Studies revealed the unprecedented sulfur-containing heterocycles bound to ferrocene units. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5825 / 5828
页数:4
相关论文
共 31 条
[1]   TOTAL SYNTHESIS OF THE NOVEL BENZOPENTATHIEPIN VARACINIUM TRIFLUOROACETATE - THE VIABILITY OF VARACIN FREE-BASE [J].
BEHAR, V ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7017-7018
[2]   TRANSFORMATION OF ISATIN WITH P4S10 TO PENTATHIEPINO[6,7-B]INDOLE IN ONE-STEP [J].
BERGMAN, J ;
STALHANDSKE, C .
TETRAHEDRON LETTERS, 1994, 35 (29) :5279-5282
[3]   SYNTHESIS, STRUCTURE, AND PROPERTIES OF PENTATHIEPINS [J].
CHENARD, BL ;
HARLOW, RL ;
JOHNSON, AL ;
VLADUCHICK, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3871-3879
[4]   VARACIN - A NOVEL BENZOPENTATHIEPIN FROM LISSOCLINUM-VAREAU THAT IS CYTOTOXIC TOWARD A HUMAN COLON-TUMOR [J].
DAVIDSON, BS ;
MOLINSKI, TF ;
BARROWS, LR ;
IRELAND, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (12) :4709-4710
[5]   CHIRALITY IN UNSYMMETRICALLY SUBSTITUTED BENZOPENTATHIEPINS - THE RESULT OF A HIGH BARRIER TO RING INVERSION [J].
DAVIDSON, BS ;
FORD, PW ;
WAHLMAN, M .
TETRAHEDRON LETTERS, 1994, 35 (39) :7185-7188
[6]   A NOVEL FLUXIONAL MOLECULE - 1,2,3-TRITHIA-[3]-FERROCENOPHANE [J].
DAVISON, A ;
SMART, JC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1969, 19 (01) :P7-&
[7]   SYNTHESIS OF VARACIN, A CYTOTOXIC NATURALLY-OCCURRING BENZOPENTATHIEPIN ISOLATED FROM A MARINE ASCIDIAN [J].
FORD, PW ;
DAVIDSON, BS .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4522-4523
[8]  
FRISCH MJ, 2001, GAUSSIAN 98 REVISION
[9]  
Hayashi T., 1995, FERROCENES
[10]   MODELS OF THE INTERACTION OF FERROCENE-1,1'-DITHIOL AND DIOLEFINS .2. ACID AND BASE-CATALYZED REACTIONS OF FERROCENETHIOLS WITH ACTIVATED OLEFINS [J].
HERBERHOLD, M ;
NUYKEN, O ;
POHLMANN, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 501 (1-2) :13-22