The one-pot synthesis and Diels-Alder reactivity of 2,5-dihydrothiophene-1,1-dioxide-3-carboxylic acid

被引：6

作者：

Andrade, GS

Berkner, JE

Liotta, CL

Eckert, C

Schiraldi, DA

Andersen, A

Collard, DM ^{[1
]}

机构：

[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

[2] Georgia Inst Technol, Sch Chem Engn, Atlanta, GA 30332 USA

[3] KoSa, Spartanburg, SC USA

[4] DuPont Co Inc, Expt Stn, Delaware, OH USA

来源：

SYNTHETIC COMMUNICATIONS | 2003年 / 33卷 / 20期

关键词：

sulfolene; carboxylation; 1,3-butadiene-2-carboxylic acid; Diels-Alder reaction;

D O I：

10.1081/SCC-120024845

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot preparation of 2,5-dihydrothiophene-1,1-dioxide-3 carboxylic acid (3-sulfolene-3-carboxylic acid) is reported. The carboxylation of 3-sulfolene, exclusively at the 3-position, using CO2 and DBU proceeds to >90% conversion. A rapid workup gives 3-sulfolene-3-carboxylic acid, a stable precursor to 1,3-butadiene-2-carboxylic acid. High conversions to Diels-Alder adducts were obtained upon treatment of 3-sulfolene-3-carboxylic acid with various dienophiles.

引用

收藏

页码：3643 / 3650

页数：8

相关论文

共 14 条

[1] PREPARATION OF METHYL-2-(OMEGA-IODOALKYL)PROPENOATES AND A FACILE ROUTE TO 2-CARBOMETHOXY-1,3-BUTADIENE [J].

ALANINE, AID ;

FISHWICK, CWG ;

JONES, AD ;

MITCHELL, MB .

TETRAHEDRON LETTERS, 1989, 30 (41) :5653-5654

[2]

BERKNER J, 1997, THESIS GEORGIA I TEC

[3] NAD(P)+-NAD(P)H MODELS .71. A CONVENIENT ROUTE TO THE SYNTHESIS OF JUVABIONE [J].

FUJII, M ;

AIDA, T ;

YOSHIHARA, M ;

OHNO, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (04) :1255-1257

[4] CHEMISTRY OF DIAZABICYCLOUNDECENE (DBU) AND OTHER PYRIMIDOAZEPINES [J].

HERMECZ, I .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1987, 42 :83-202

[5] 1,4-DIAZOBICYCLO[2.2.2]OCTANE-CATALYZED COUPLING OF ALDEHYDES AND ACTIVATED DOUBLE-BONDS .3. A SHORT AND PRACTICAL SYNTHESIS OF MIKANECIC ACID (4-VINYL-1-CYCLOHEXENE-1,4-DICARBOXYLIC ACID) [J].

HOFFMANN, HMR ;

RABE, J .

HELVETICA CHIMICA ACTA, 1984, 67 (02) :413-415

[6] Polar, functionalized diene-based materials. 1. Bulk, solution, and emulsion free radical polymerization of 2-cyanomethyl-1,3-butadiene [J].

Jing, Y ;

Sheares, VV .

MACROMOLECULES, 2000, 33 (17) :6255-6261

[7] NEW SYNTHESIS OF METHYL 1,3-BUTADIENE-2-CARBOXYLATE BY THE CHELETROPIC EXTRUSION OF CARBON-MONOXIDE FROM 3-CARBOMETHOXY-3,4-PENTADIENAL AND A STUDY OF ITS DIMERIZATION TO GIVE DIMETHYL MIKANECATE (DIMETHYL 4-ETHENYL-1-CYCLOHEXENE-1,4-DICARBOXYLATE) [J].

JUNG, ME ;

ZIMMERMAN, CN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7813-7814

[8]

MANDAI T, 1980, J CHEM LETT, P1057

[9]

MARTINA D, 1982, TETRAHEDRON LETT, V23, P862

[10] DIHYDROTHIOPHENES .7. SYNTHESIS OF 3-CARBOXYLATED 2,5-DIHYDROTHIOPHENES [J].

MCINTOSH, JM ;

SIELER, RA .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (02) :226-231