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Fluoride-Promoted Rearrangement of Organo Silicon Compounds: A New Synthesis of 2-(Arylmethyl)aldehydes from 1-Alkynes

Laura Antonella Aronica, Patrizio Raffa, Anna Maria Caporusso and Piero Salvadori*

*Dipartimento di Chimica e Chimica Industriale, UniversitÓ degli Studi di Pisa, Via Risorgimento 35, 56126 Pisa, Italy, Email: psalvadcci.unipi.it

L. A. Aronica, P. Raffa, A. M. Caporusso, P. Salvadori, J. Org. Chem., 2003, 5, 9292-9298.

DOI: 10.1021/jo0351062


Abstract

A new approach to 2-(arylmethyl)aldehydes begins with a silylformylation reaction of terminal acetylenes with aryl- or heteroarylsilanes, followed by treatment of the products with TBAF to induce a 1,2-anionotropic rearrangement of the aryl group.

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proposed mechanism



Key Words

2-Arylmethylaldehydes, Arenes, Vinylsilanes, Carbonylation, Rearrangement


ID: J42-Y2003-1070