A CRYSTALLINE 7-MEMBERED CYCLIC KETENE IMINE FROM A THIOCARBONYL S-METHYLIDE

被引：33

作者：

HUISGEN, R ^{[1
]}

LANGHALS, E ^{[1
]}

NOTH, H ^{[1
]}

机构：

[1] UNIV MUNICH,INST ANORGAN CHEM,W-8000 MUNICH 2,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 05期

关键词：

D O I：

10.1021/jo00292a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3 + 4] cycloaddition of 1,1,3,3-tetramethylindane-2-thione S-methylide (11) and 2,3-bis(trifluoromethyl)fumaronitrile (2c) afforded 86% of the ketene imine 14, the X-ray structure of which revealed a strained ring; the thermolysis to thione 9 + cyclopropane 18 constitutes a novel reaction course. © 1990 American Chemical Society.

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页码：1412 / 1414

页数：3

相关论文

共 11 条

[1] SYNTHESIS AND CONFIGURATIONAL STABILITY OF 3,8-DIBENZYL-1-AZACYCLO-OCTA-1,2-DIENE - THE 1ST 8-MEMBERED CYCLIC KETENIMINE [J].

FIRL, J ;

SCHINK, K ;

KOSBAHN, W .

CHEMISTRY LETTERS, 1981, (04) :527-530

[2] THE 1ST 2-STEP 1,3-DIPOLAR CYCLOADDITIONS - INTERCEPTION OF AN INTERMEDIATE [J].

HUISGEN, R ;

MLOSTON, G ;

LANGHALS, E .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (21) :4085-4087

[3] A STABLE 7-MEMBERED RING KETENE IMINE FROM A THIOCARBONYL YLIDE AND AN ACCEPTOR OLEFIN [J].

HUISGEN, R ;

LANGHALS, E ;

MLOSTON, G ;

OSHIMA, T .

HETEROCYCLES, 1989, 29 (11) :2069-2074

[4] RING CONTRACTION OF A CYCLIC 7-MEMBERED KETENE IMINE [J].

HUISGEN, R ;

LANGHALS, E ;

OSHIMA, T .

HETEROCYCLES, 1989, 29 (11) :2075-2078

[5] 1ST 2-STEP 1,3-DIPOLAR CYCLOADDITIONS - NONSTEREOSPECIFICITY [J].

HUISGEN, R ;

MLOSTON, G ;

LANGHALS, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6401-6402

[6]

JOCHIMS JC, 1984, TETRAHEDRON, V40, P893, DOI 10.1016/S0040-4020(01)91479-6

[7] KETENIMINES - GEOMETRY AND BARRIERS TO RACEMIZATION [J].

JOCHIMS, JC ;

ANET, FAL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5524-&

[8] 1,3-CYCLOADDITIONS OF ALIPHATIC THIONE S-METHYLIDES TO DIMETHYL 2,3-DICYANO-FUMARATE AND 2,3-DICYANOMALEATE - A TEST CASE FOR STERIC COURSE AND MECHANISM [J].

MLOSTON, G ;

LANGHALS, E ;

HUISGEN, R .

TETRAHEDRON LETTERS, 1989, 30 (39) :5373-5376

[9] STEREOCHEMISTRY OF MOLECULES CONTAINING C=C=N GROUP .4. X-RAY DETERMINATION OF MOLECULAR STRUCTURE OF N-PARA-TOLYL-2,2-DIPHENYLVINYLIDENAMINE AND N-PARA BROMOPHENYL-2,2-DIPHENYLVINYL-IDENAMINE [J].

NAQVI, RR ;

WHEATLEY, PJ .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1970, (12) :2053-&

[10] STEREOCHEMISTRY OF CYCLOADDITION REACTION OF 1,2-BIS (TRIFLUOROMETHYL)-1,2-DICYANOETHYLENE AND ELECTRON-RICH ALKENES [J].

PROSKOW, S ;

SIMMONS, HE ;

CAIRNS, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (22) :5254-&