Highly Wolff Selective Rh(II) Catalysed Decomposition of α-Diazo- β-Ketophosphonates Having an Oxygen Atom Adjacent to the γ-Position

Mohamed      Boukraa; Wissam      Dayoub; Alain      Doutheau

doi:10.2174/157017806775789877

Abstract

α-Diazo-β-ketophosphonates, bearing an oxygen atom adjacent to the γ position, led mainly or exclusively to compounds derived from a Wolff rearrangement when submitted to the action of a catalytic amount of Rh(II) in refluxing toluene. It is suggested that the presence of this inductive withdrawing electronic atom prevents competing intramolecular C-H insertion reactions to occur.

Keywords: Ketenes, Wolff rearrangement, Rhodiocarbenoid, α-Diazo-β-keto-compounds

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Letters in Organic Chemistry

Title: Highly Wolff Selective Rh(II) Catalysed Decomposition of α-Diazo- β-Ketophosphonates Having an Oxygen Atom Adjacent to the γ-Position

Volume: 3 Issue: 3

Author(s): Mohamed Boukraa, Wissam Dayoub and Alain Doutheau

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Keywords: Ketenes, Wolff rearrangement, Rhodiocarbenoid, α-Diazo-β-keto-compounds

Abstract: α-Diazo-β-ketophosphonates, bearing an oxygen atom adjacent to the γ position, led mainly or exclusively to compounds derived from a Wolff rearrangement when submitted to the action of a catalytic amount of Rh(II) in refluxing toluene. It is suggested that the presence of this inductive withdrawing electronic atom prevents competing intramolecular C-H insertion reactions to occur.

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Boukraa Mohamed, Dayoub Wissam and Doutheau Alain, Highly Wolff Selective Rh(II) Catalysed Decomposition of α-Diazo- β-Ketophosphonates Having an Oxygen Atom Adjacent to the γ-Position, Letters in Organic Chemistry 2006; 3 (3) . https://dx.doi.org/10.2174/157017806775789877