THE 1ST SYNTHESIS OF ALIPHATIC SULFINES FROM THIONO-ESTERS

被引：19

作者：

LEMARIE, M ^{[1
]}

PHAM, TN ^{[1
]}

METZNER, P ^{[1
]}

机构：

[1] INST SCI MAT & RAYONNEMENT,CNRS,CHIM COMPOSES THIOORGAN LAB,6 BLVD MARECHAL JUIN,F-14050 CAEN,FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 50期

关键词：

D O I：

10.1016/0040-4039(91)80120-U

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of various thiono-esters with one equivalent of meta-chloroperoxybenzoic acid at 0-degrees-C in dichloromethane furnishes the corresponding sulfines, evidenced for the first time. These thiocarbonyl oxides are rather unstable at room temperature and give carboxylic esters, with loss of sulfur. The overall sequence provides an easy and quantitative C = S --> C = O transformation.

引用

收藏

页码：7411 / 7414

页数：4

相关论文

共 18 条

[1] PERACID OXIDATION OF BENZOTHIOPYRANTHIONES AND BENZOPYRANTHIONES [J].

BUGGLE, K ;

FALLON, B .

MONATSHEFTE FUR CHEMIE, 1987, 118 (10) :1197-1199

[2] DIFLUORINATION OF ESTERS - PREPARATION OF ALPHA,ALPHA-DIFLUORO ETHERS [J].

BUNNELLE, WH ;

MCKINNIS, BR ;

NARAYANAN, BA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :768-770

[3] THIOIMIDATE N-OXIDES - NITRONES OF THIO ESTERS [J].

COATES, RM ;

FIRSAN, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5198-5209

[4]

COREY EJ, 1986, TETRAHEDRON LETT, V25, P2639

[5] DIRECT SYNTHESIS OF SULFINES BY OXIDATION OF ENETHIOLIZABLE THIOKETONES [J].

LENOCHER, AM ;

METZNER, P .

TETRAHEDRON LETTERS, 1991, 32 (06) :747-750

[6] A FACILE ENTREE TO ALPHA-OXO SULFINES BY REACTION OF THIONYL CHLORIDE WITH SILYL ENOL ETHERS [J].

LENZ, BG ;

REGELING, H ;

ZWANENBURG, B .

TETRAHEDRON LETTERS, 1984, 25 (51) :5947-5948

[7] KETENE ACETALS .21. THE DEALCOHOLATION OF ORTHOESTERS - DIMETHYLKETENE DIMETHYLACETAL [J].

MCELVAIN, SM ;

VENERABLE, JT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (04) :1661-1669

[8] SYNTHESIS OF SULFINES FROM ALIPHATIC DITHIOESTERS AND THEIR REARRANGEMENT TO DITHIOPEROXYESTERS [J].

METZNER, P ;

PHAM, TN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (05) :390-391

[9]

METZNER P, 1991, PHOSPHORUS SULFUR, V59, P1

[10]

METZNER P, IN PRESS SYNTHESIS