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

Authors
ARMESTO D GALLEGO MG HORSPOOL WM AGARRABEITIA AR
Citation
D. Armesto et al., A NEW PHOTOCHEMICAL-SYNTHESIS OF CYCLOPROPANECARBOXYLIC ACIDS PRESENTIN PYRETHROIDS BY THE AZA-DI-PI-METHANE REARRANGEMENT, Tetrahedron, 51(33), 1995, pp. 9223-9240
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
33
Year of publication
1995
Pages
9223 - 9240
Database
ISI
SICI code
0040-4020(1995)51:33<9223:ANPOCA>2.0.ZU;2-1
Abstract
A novel synthetic route to chrysanthemic acid, entylidenmethyl-3,3-dim ethylcyclopropanecarboxylic acid, fluorenespiro-2,2-dimethylcyclopropa necarboxylic acid and indenespiro-2,2-dimethylcyclopropanecarboxylic a cid, 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.