THEORETICAL APPROACH AND FIRST EXAMPLES OF N-ACYL-THIOFORMAMIDES AS DIENOPHILES IN THE DIELS-ALDER REACTION

被引：11

作者：

ARNAUD, R ^{[1
]}

CHAVANT, PY ^{[1
]}

MOLVINGER, K ^{[1
]}

VALLEE, Y ^{[1
]}

机构：

[1] UNIV GRENOBLE 1,LEDSS,CNRS LAB,F-38041 GRENOBLE,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 18期

关键词：

D O I：

10.1039/c39950001897

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

ab initio Calculations as well as experimental results show that the C = S bond of a thioamide can act as a dienophile in the Diels-Alder reaction provided that the nitrogen atom is substituted by pi-acceptor groups.

引用

页码：1897 / 1898

页数：2

共 27 条

[1] FACILE INTRAMOLECULAR CYCLOADDITIONS OF 2-(N-ACYLAMINO)-1-THIA-1,3-DIENES [J].

BARNISH, IT ;

FISHWICK, CWG ;

HILL, DR .

TETRAHEDRON LETTERS, 1991, 32 (03) :405-408

[2] DITHIOESTERS AS HETERO-DIENOPHILES IN DIELS-ALDER CYCLOADDITION - SYNTHESIS OF 6-ALKYLTHIO-5,6-DIHYDRO-2H-THIOPYRANS [J].

BESLIN, P ;

METZNER, P .

TETRAHEDRON LETTERS, 1980, 21 (48) :4657-4658

[3] ETHYL AND METHYL THIOXOACETATES, DIENOPHILIC THIOALDEHYDES FORMED FROM SULFENYL CHLORIDES BY 1,2-ELIMINATION [J].

BLADON, CM ;

FERGUSON, IEG ;

KIRBY, GW ;

LOCHEAD, AW ;

MCDOUGALL, DC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07) :1541-1545

[4] EFFICIENT DIFFUSE FUNCTION-AUGMENTED BASIS SETS FOR ANION CALCULATIONS. III. THE 3-21+G BASIS SET FOR FIRST-ROW ELEMENTS, LI-F [J].

CLARK, T ;

CHANDRASEKHAR, J ;

SPITZNAGEL, GW ;

SCHLEYER, PV .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (03) :294-301

[5] TOWARD A SYSTEMATIC MOLECULAR-ORBITAL THEORY FOR EXCITED-STATES [J].

FORESMAN, JB ;

HEADGORDON, M ;

POPLE, JA ;

FRISCH, MJ .

JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (01) :135-149

[6] PREPARATION AND CHEMISTRY OF THE DIELS-ALDER ADDUCTS OF LEVOPIMARIC ACID AND ACTIVATED THIOCARBONYL DIENOPHILES [J].

FRIEDRICH, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2442-2446

[7] DIELS-ALDER REACTIONS OF CYANOTHIOFORMAMIDES [J].

FRIEDRICH, K ;

ZAMKANEI, M .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (05) :1867-1872

[8]

FRIEDRICH K, 1977, TETRAHEDRON LETT, V18, P2139

[9]

Frisch M.J., 1992, GAUSSIAN 92 REVISION

[10]

GLENDENING ED, 1983, J PHYS CHEM-US, V82, P2679

← 1 2 3 →