AN EFFECTIVE AND SELECTIVE SYNTHESIS OF STERICALLY CROWDED BENZOTRITHIOLES FROM BENZODITHIASTANNOLES VIA BENZOTRITHIOLE 2-OXIDES

被引:34
作者
OGAWA, S [1 ]
YOMOJI, N [1 ]
CHIDA, S [1 ]
SATO, R [1 ]
机构
[1] IWATE UNIV, FAC ENGN, DEPT APPL CHEM & MOLEC SCI, MORIOKA, IWATE 020, JAPAN
关键词
D O I
10.1246/cl.1994.507
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sterically crowded benzotrithioles were efficiently and selectively prepared by the reduction of corresponding benzotrithiole 2-oxides which were readily obtained on treatment of benzodithiastannoles, synthetic equivalents of benzenedithiols, with thionyl chloride.
引用
收藏
页码:507 / 510
页数:4
相关论文
共 28 条
[1]   FACILE FORMATION OF 1,2-DITHIONE AND 1,2-SELENOXOTHIONE BY THE PHOTOLYSIS OF FUSED CYCLOPOLYSULFIDES [J].
ANDO, W ;
KUMAMOTO, Y ;
TOKITOH, N .
TETRAHEDRON LETTERS, 1987, 28 (41) :4833-4836
[2]   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
[3]   ORTHO-LITHIOTHIOPHENOL EQUIVALENTS - GENERATION, REACTIONS, AND APPLICATIONS IN SYNTHESIS OF HINDERED THIOLATE LIGANDS [J].
BLOCK, E ;
ESWARAKRISHNAN, V ;
GERNON, M ;
OFORIOKAI, G ;
SAHA, C ;
TANG, K ;
ZUBIETA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :658-665
[4]   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
[5]   BENZOPENTATHIEPINS - SYNTHESIS VIA THERMOLYSIS OF BENZOTHIADIAZOLES WITH SULFUR [J].
CHENARD, BL ;
MILLER, TJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (07) :1221-1224
[6]   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
[7]   X-RAY CRYSTAL-STRUCTURE OF 13,14,15-TRITHIAPENTACYCLO[9.5.1.13,9.04,8.012,16]-OCTADEC-5-ENE [J].
EMSLEY, J ;
GRIFFITHS, DW ;
OSBORN, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (15) :658-658
[8]  
FEHER F, 1972, Z NATURFORSCH PT B, VB 27, P1006
[9]  
FEHER F, 1971, TETRAHEDRON LETT, P2125
[10]   DIRECTED ORTHO-LITHIATION OF LITHIUM THIOPHENOLATE - NEW METHODOLOGY FOR THE PREPARATION OF ORTHO-SUBSTITUTED THIOPHENOLS AND RELATED-COMPOUNDS [J].
FIGULY, GD ;
LOOP, CK ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :654-658