PHTHALIMIDOSULFENYL CHLORIDE .5. REACTION WITH ENOLIZABLE CARBONYL-COMPOUNDS AND SYNTHESIS OF FUNCTIONALIZED THIONES

被引:52
作者
CAPOZZI, G [1 ]
MENICHETTI, S [1 ]
NATIVI, C [1 ]
ROSI, A [1 ]
VALLE, G [1 ]
机构
[1] UNIV PADUA,DIPARTIMENTO CHIM ORGAN,CNR,CTR BIOPOLIMERI,I-35100 PADUA,ITALY
关键词
PHTHALIMIDOSULPHENYL CHLORIDE REACTIONS WITH CARBONYL COMPOUNDS; SYNTHESIS AND CYCLOADDITIONS OF THIONES; SYNTHESIS OF 1-PHENYL-1-HYDROXYETHANTHIOLE;
D O I
10.1016/S0040-4020(01)82000-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Beta-ketothio derivatives 4, prepared by reaction of phthalimidosulphenyl chloride with enolizable carbonyl compounds, afford, in presence of pyridine, unstable functionalized thiones which can be trapped with 1,3-dienes to give the corresponding cycloaddition products 8 and 9.
引用
收藏
页码:9023 / 9032
页数:10
相关论文
共 14 条
[1]   PREPARATION OF EPISULFIDES FROM ALKENES VIA SUCCINIMIDE-N-SULFENYL CHLORIDE OR PHTHALIMIDE-N-SULFENYL CHLORIDE ADDUCTS [J].
BOMBALA, MU ;
LEY, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12) :3013-3016
[2]   GENERATION OF THIONITROSOARENES (ARN=S) FROM N-(ARYLAMINOTHIO)PHTHALIMIDES AND INSITU TRAPPING WITH ALKENES AND CONJUGATED DIENES [J].
BRYCE, MR ;
TAYLOR, PC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (12) :3225-3235
[3]  
BUSI E, 1992, SYNTHESIS-STUTTGART, P643
[4]   PHTHALIMIDESULFENYL CHLORIDE .4. ADDITION TO ACETYLENES AND SYNTHETIC UTILIZATION OF THEIR ADDUCTS [J].
CAPOZZI, G ;
GORI, L ;
MENICHETTI, S ;
NATIVI, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (15) :1923-1928
[5]   PHTHALIMIDOSULPHENYL CHLORIDE - A SYNTHETIC EQUIVALENT OF INACCESSIBLE SULFENYL CHLORIDES [J].
CAPOZZI, G ;
GORI, L ;
MENICHETTI, S .
TETRAHEDRON LETTERS, 1990, 31 (43) :6213-6216
[6]   PHTHALIMIDOSULPHENYL CHLORIDE .2. SYNTHESIS OF UNUSUAL THIIRANE DERIVATIVES [J].
CAPOZZI, G ;
GORI, L ;
MENICHETTI, S .
TETRAHEDRON, 1991, 47 (34) :7185-7196
[7]  
Capozzi G., 1990, CHEM SULPHENIC ACIDS, P403
[8]   SILICON-ASSISTED SYNTHESIS OF THIOCARBONYL DERIVATIVES AND REACTIVITY OF DIENOPHILIC THIOALDEHYDES [J].
CAPPERUCCI, A ;
DEGL'INNOCENTI, A ;
RICCI, A ;
MORDINI, A ;
REGINATO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) :7323-7328
[9]   STUDIES IN ORGANIC SULFUR COMPOUNDS .7. LITHIUM ALUMINUM HYDRIDE REDUCTION OF XANTHATES TO MERCAPTANS - SYNTHESIS OF SUBSTITUTED BETA-MERCAPTOETHANOLS [J].
DJERASSI, C ;
GORMAN, M ;
MARKLEY, FX ;
OLDENBURG, EB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (03) :568-571
[10]   THIATION REACTIONS OF SOME ACTIVE CARBONYL-COMPOUNDS WITH SULFUR TRANSFER REAGENTS [J].
HUANG, NZ ;
LAKSHMIKANTHAM, MV ;
CAVA, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :169-172