A NOVEL SYNTHESIS OF THIOPHENES FROM ALLENIC SULFONES INVOLVING ALPHA,BETA-UNSATURATED SULFINES AS INTERMEDIATES

被引：13

作者：

BRAVERMAN, S ^{[1
]}

VANASTEN, PFTM ^{[1
]}

VANDERLINDEN, JB ^{[1
]}

ZWANENBURG, B ^{[1
]}

机构：

[1] CATHOLIC UNIV NIJMEGEN, DEPT ORGAN CHEM, NSR CTR MOLEC STRUCT DESIGN & SYNTH, 6525 ED NIJMEGEN, NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)79399-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the synthesis of alpha,beta-unsaturated sulfines by a Peterson alkylidenation of sulfur dioxide is described. The required alpha-silyl carbanions are generated by heteroconjugate addition of alkyllithium to alpha-trimethylsilylated allenic sulfones. The conjugated vinylsulfines thus prepared undergo a rapid and unprecedented cycloaromatization to thiophene derivatives. A mechanism for this remarkable conversion is presented.

引用

下载

页码：3867 / 3870

页数：4

共 50 条

[21] Efficient synthesis of indolizidine alkaloids from gamma-hydroxy-alpha,beta-unsaturated sulfones
Carretero, JC
Arrayas, RG
DeGracia, IS
Adrio, J
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 120 : 347 - 348
[22] FACILE SYNTHESIS OF E-GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFONES FROM ALDEHYDES
DOMINGUEZ, E
CARRETERO, JC
TETRAHEDRON LETTERS, 1990, 31 (17) : 2487 - 2490
[23] STEREOCHEMISTRY OF THE ELECTROPHILIC FRAGMENTATION-CYCLIZATION OF ALLENIC SULFONES AND SULFINATES - STEREOSELECTIVE SYNTHESIS OF CHIRAL ALPHA,BETA-UNSATURATED GAMMA-SULTINES
BRAVERMAN, S
DUAR, Y
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (04) : 1061 - 1063
[24] METALATION OF PROPARGYLIC AND ALLENIC ETHERS SYNTHESIS OF ALPHA, BETA-UNSATURATED CARBONYL-COMPOUNDS
LEROUX, Y
ROMAN, C
TETRAHEDRON LETTERS, 1973, (28) : 2585 - 2586
[25] SULFONES .2. ALKENES, DIENES, ALPHA,BETA-UNSATURATED SULFONES, AND MONOSULFONES FROM BETA-DISULFONES
CRONYN, MW
ZAVARIN, E
JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (02): : 139 - 154
[26] A CONVENIENT ONE-POT SYNTHESIS OF ALPHA-FUNCTIONALIZED ALPHA, BETA-UNSATURATED SULFONES
LEE, JW
OH, DY
SYNTHETIC COMMUNICATIONS, 1990, 20 (02) : 273 - 277
[27] NOVEL STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA, BETA-UNSATURATED AND (Z)-ALPHA, BETA-UNSATURATED CARBOXYLIC ESTERS VIA HYDROBORATION
NEGISHI, EI
LEW, G
YOSHIDA, T
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15): : 2321 - 2322
[28] A NOVEL SYNTHESIS OF BETA-PERFLUOROALKYLATED ALPHA,BETA-UNSATURATED NITRILES
SHEN, YC
WANG, TL
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02): : 487 - 488
[29] PHASE-TRANSFER CATALYZED CONDENSATION OF SULFONES WITH ALDEHYDES IN AN AQUEOUS SYSTEM - SYNTHESIS OF ALPHA,BETA-UNSATURATED SULFONES
CARDILLO, G
SAVOIA, D
UMANIRONCHI, A
SYNTHESIS-STUTTGART, 1975, (07): : 453 - 455
[30] A SYNTHESIS OF ALPHA,BETA-UNSATURATED AMIDES
GALAT, A
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (07) : 2596 - 2596

← 1 2 3 4 5 →