A NEW PHOTOCHEMICAL-SYNTHESIS OF CYCLOPROPANECARBOXYLIC ACIDS PRESENT IN PYRETHROIDS BY THE AZA-DI-PI-METHANE REARRANGEMENT

被引：22

作者：

ARMESTO, D

GALLEGO, MG

HORSPOOL, WM

AGARRABEITIA, AR

机构：

[1] Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense

来源：

TETRAHEDRON | 1995年 / 51卷 / 33期

关键词：

D O I：

10.1016/0040-4020(95)00527-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthetic route to chrysanthemic acid, 2-cyclopentylidenmethyl-3,3-dimethylcyclopropanecarboxylic acid, fluorenespiro-2,2-dimethylcyclopropanecarboxylic acid and indenespiro-2,2-dimethylcyclopropanecarboxylic acid, all of them present in pyrethroids of known insecticidal activity, is described. The key step in the synthesis is the aza-di-pi-methane rearrangement of some 1-aza-1,4,6-trienes and some 1-aza-1,4-dienes, using tripler sensitization.

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页码：9223 / 9240

页数：18

相关论文

共 20 条

[1] SYNTHESES OF PYRETHROID ACIDS [J].

ARLT, D ;

JAUTELAT, M ;

LANTZSCH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (09) :703-722

[2] PHOTOCHEMISTRY OF BETA,GAMMA-UNSATURATED OXIME ACETATES - AZA-DI-PI-METHANE REACTIVITY OF FUNCTIONALIZED ALL-ALIPHATIC SYSTEMS - A PHOTOCHEMICAL APPROACH TO PYRETHRIN-LIKE CYCLOPROPANE DERIVATIVES [J].

ARMESTO, D ;

GALLEGO, MG ;

HORSPOOL, WM .

TETRAHEDRON, 1990, 46 (17) :6185-6192

[3] EXTENSION OF THE AZA-DI-PI-METHANE REACTION TO STABLE DERIVATIVES - PHOTOCHEMICAL CYCLIZATION OF BETA,GAMMA-UNSATURATED OXIME ACETATES [J].

ARMESTO, D ;

HORSPOOL, WM ;

LANGA, F ;

RAMOS, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :223-228

[4] PHOTOCHEMICAL-SYNTHESIS OF OXIME ACETATES DERIVATIVES OF 1-CARBALDEHYDOBICYCLO[N.1.0]ALKANES BY THE AZA-DI-PI-METHANE REARRANGEMENT [J].

ARMESTO, D ;

RAMOS, A .

TETRAHEDRON, 1993, 49 (32) :7159-7168

[5] STERIC AND ELECTRONIC EFFECTS ON THE PHOTOCHEMICAL REACTIVITY OF OXIME ACETATES OF BETA,GAMMA-UNSATURATED ALDEHYDES [J].

ARMESTO, D ;

HORSPOOL, WM ;

GALLEGO, MG ;

AGARRABEITIA, AR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01) :163-169

[6] A STUDY OF THE COMPETITION BETWEEN THE DI-PI-METHANE AND THE AZADI-PI-METHANE PROCESSES IN 2-VINYL-BETA,GAMMA-UNSATURATED OXIME DERIVATIVES - THE NOVEL AZADI-PI-METHANE REACTIVITY OF GAMMA-UNSATURATED OXIMES [J].

ARMESTO, D ;

ORTIZ, MJ ;

RAMOS, A ;

HORSPOOL, WM ;

MAYORAL, EP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8115-8124

[7]

ARMESTO D, 1991, Patent No. 9100648

[8] PHOTO-CHEMICAL FORMATION OF CHRYSANTHEMIC ACID AND CYCLOPROPYLACRYLIC ACID-DERIVATIVES - CASE OF MULTIPLICITY-DEPENDENT REGIO-SPECIFICITY IN DI-PI-METHANE REARRANGEMENT [J].

BAECKSTROM, P .

TETRAHEDRON, 1978, 34 (22) :3331-3335

[9] COMPLETE KINETIC-ANALYSIS OF THERMAL STEREOMUTATIONS AMONG THE 8 2,3-DIDEUTERIO-2-(METHOXYMETHYL)SPIRO[CYCLOPROPANE-1,1'-INDENES] [J].

BALDWIN, JE ;

BLACK, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1029-1040

[10] PHOTOCHEMICAL DI-PI-METHANE REARRANGEMENT LEADING TO METHYL CHRYSANTHEMATE [J].

BULLIVANT, MJ ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (03) :256-258