GENERATION AND TRAPPING OF ORTHO-SUBSTITUTED THIONITROSOBENZENES - COMPETITIVE DIELS-ALDER AND ENE REACTIONS WITH DIMETHYLBUTADIENE

被引：7

作者：

BRYCE, MR

HEATON, JN

机构：

[1] Department of Chemistry, University of Durham, Durham

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 50期

关键词：

D O I：

10.1016/0040-4039(91)80134-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transient thionitrosoarenes, ArN = S, (2) that bear a substituent (CN, Br or Me) ortho to the reactive N = S group have been generated by two entirely different routes and intercepted with dimethylbutadiene to afford mixtures of Diels-Alder and ene adducts, (3) and (4), respectively; the ene adduct predominates for each system.

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页码：7459 / 7462

页数：4

相关论文

共 14 条

[1] THE STEREOCHEMICAL OUTCOME OF DIENE ADDITIONS TO THIONITROSOARENES (ARN=S) [J].

BRYCE, MR ;

TAYLOR, PC .

TETRAHEDRON LETTERS, 1989, 30 (29) :3835-3836

[2] EFFICIENT GENERATION OF THIONITROSOARENES (ARN=S) BY FRAGMENTATION OF N-(ARYLAMINOTHIO)PHTHALIMIDES [J].

BRYCE, MR ;

TAYLOR, PC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (14) :950-951

[3] GENERATION OF THIONITROSOARENES (ARN=S) FROM N-(ARYLAMINOTHIO)PHTHALIMIDES AND INSITU TRAPPING WITH ALKENES AND CONJUGATED DIENES [J].

BRYCE, MR ;

TAYLOR, PC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (12) :3225-3235

[4]

Carruthers W., 1990, CYCLOADDITION REACTI

[5] C-NITROSOFORMAMIDES, A NEW CLASS OF TRANSIENT DIENOPHILES FORMED BY OXIDATION OF N-HYDROXYUREAS [J].

CHRISTIE, CC ;

KIRBY, GW ;

MCGUIGAN, H ;

MACKINNON, JWM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2469-2473

[6] ENE REACTION [J].

HOFFMANN, HM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :556-&

[7] ENE REACTIONS OF CONJUGATED DIENES .2. DEPENDENCE OF RATE ON DEGREE OF HYDROGEN REMOVED AND S-CIS OR S-TRANS DIENE CHARACTER [J].

JACOBSON, BM ;

ARVANITIS, GM ;

ELIASEN, CA ;

MITELMAN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :194-201

[8] GENERATION OF THIONITROSO COMPOUNDS BY BENZISOTHIAZOLE RING-OPENING [J].

JOUCLA, MF ;

REES, CW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (06) :374-375

[9]

KLIMOVA E, 1968, DOKL AKAD NAUK SSSR+, V180, P865

[10] CYCLOADDITION REACTIONS OF THIOPHENE S,N-YLIDES - A NOVEL ROUTE TO THIONITROSO COMPOUNDS [J].

METHCOHN, O ;

VANVUUREN, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (17) :1144-1146