Tetrahedron

Chemoselectivity in the rhodium (II) acetate catalysed decomposition of α-diazo-β-keto-γ, δ-alkenyl-δ-aryl compounds: Aromatic CH insertion reaction or wolff …

D Collomb, B Chantegrel, C Deshayes

Index: Collomb, Didier; Chantegrel, Bernard; Deshayes, Christian Tetrahedron, 1996 , vol. 52, # 31 p. 10455 - 10472

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Citation Number: 18

Abstract

The rhodium (II) acetate catalysed decomposition of α-diazo-β-keto-γ, δ-alkenyl phosphonates 1 substituted in the δ-position by an aryl group gave rise to mixtures of isomeric hydroxynaphthalenephosphonates, 3 resulting from a Wolff rearrangement- electrocyclization process and 5 resulting from an aromatic CH insertion reaction. The 3: 5 ratio was found to depend on the substitution pattern of the γ, δ-double bond. The ...