Tetrahedron

A new photochemical synthesis of cyclopropanecarboxylic acids present in pyrethroids by the aza-di-π-methane rearrangement

…, MG Gallego, WM Horspool, AR Agarrabeitia

Index: Armesto, Diego; Gallego, Mar G.; Horspool, William M.; Agarrabeitia, Antonia R. Tetrahedron, 1995 , vol. 51, # 33 p. 9223 - 9240

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Citation Number: 29

Abstract

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-n-rnethane rearrangement of some 1-aza-1, 4, 6-trienes and some 1-aza-1, 4- ...