Reaction of polymerization-resistant 1,2-dithiolanes with lithiated picolines: Simple ring opening and 1,3-dithiane formation

被引:5
作者
Tazaki, M [1 ]
Okai, S [1 ]
Hieda, T [1 ]
Nagahama, S [1 ]
Takagi, M [1 ]
机构
[1] KYUSHU UNIV,FAC ENGN,DEPT CHEM SCI & TECHNOL,HIGASHI KU,FUKUOKA 812,JAPAN
来源
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1996年 / 112卷 / 1-4期
关键词
1,2-dithiolane; nucleophilic S-S bond cleavage; lithiated picolines; mono-S-picolyl-1,3-propanedithiols; ligands for transition metals; 1,3-dithianes;
D O I
10.1080/10426509608046352
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reaction of polymerization resistant 1,2-dithiolanes 1 with excess pyridylmethyllithiums 3 in THF gave the corresponding ring-opened products 2 in good yields, but the by-products 2-pyridyl-1,3-dithianes 5 and 1,3-propanedithiols 6 could not be excluded. Addition of hexamethylphosphoric triamide (HMPT) to the reaction mixture resulted in the selective formation of 5.
引用
收藏
页码:101 / 108
页数:8
相关论文
共 12 条
[1]  
AGER DJ, 1987, UMPOLED SYNTHONS, pCHI
[2]  
BABA Y, 1990, SOLVENT EXTRACTION A, V7, P351
[3]  
BERGSON G, 1964, ARK KEMI, V22, P475
[4]   ACIDITY MEASUREMENTS ON PYRIDINES IN TETRAHYDROFURAN USING LITHIATED SILYLAMINES [J].
FRASER, RR ;
MANSOUR, TS ;
SAVARD, S .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) :3232-3234
[5]   SOLVENT-EXTRACTION OF MERCURY(II) WITH SOME SULFUR-CONTAINING EXTRACTING REAGENTS [J].
INOUE, K ;
YASUKAWA, R ;
MIURA, N ;
BABA, Y ;
YOSHIZUKA, K .
SOLVENT EXTRACTION AND ION EXCHANGE, 1992, 10 (05) :769-785
[6]   REDUCTIVE PHOSPHORYLATION OF 1,2-DITHIOLANES WITH DIALKYL PHOSPHITES [J].
TAZAKI, M ;
NAGAHAMA, S ;
TAKAGI, M .
CHEMISTRY LETTERS, 1988, (10) :1619-1622
[7]   S-S BOND-CLEAVAGE OF POLYMERIZATION RESISTANT 1,2-DITHIOLANES BY ACETYLIDES - INTRINSIC REACTIVITY OF ENZYME-BOUND LIPOIC ACID TOWARD STABLE, LOCALIZED CARBANIONS [J].
TAZAKI, M ;
KUMAKURA, M ;
NAGAHAMA, S ;
TAKAGI, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (17) :1763-1764
[8]   REACTION OF 4,4-DIETHYL-1,2-DITHIOLANE WITH GRIGNARD-REAGENTS [J].
TAZAKI, M ;
NAGAHAMA, S ;
TAKAGI, M .
CHEMISTRY LETTERS, 1988, (08) :1339-1342
[9]   4,4-DISUBSTITUTED 1,2-DITHIOLANES AS SIMPLE-MODELS FOR ENZYME-BOUND LIPOIC ACID [J].
TAZAKI, M ;
TANABE, H ;
NAGAHAMA, S ;
TAKAGI, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :291-292
[10]   REACTION OF 1,2-DITHIOLANE WITH ALPHA-LITHIATED THIOPHENES - SELECTIVE SYNTHESES OF MONO-S-THIENYL-1,3-PROPANEDITHIOLS [J].
TAZAKI, M ;
TANABE, H ;
HIEDA, T ;
NAGAHAMA, S ;
INOUE, K ;
TAKAGI, M .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 88 (1-4) :189-193