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The first nucleophilic aromatic substitution of suitably activated 2-methoxyfurans with Grignard reagents

✍ Scribed by M.Rosaria Iesce; M.Liliana Graziano; Flavio Cermola; Stefania Montella; Lucrezia Di Gioia

Book ID: 104254067
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 126 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01430-8

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✦ Synopsis

The reaction of 2-methoxyfuroates 1 with Grignard reagents 2 leads to tertiary alcohols or S N Ar products depending on the position of the alkoxycarbonyl group. OMe-Displacement occurs only for 3-substituted derivatives. It takes place even for 3-acetyl-2-methoxyfuran while the presence of a further ester function at 4 position induces the formation of the sole 4-tertiary alcohol. The OMe-substitution has been verified for a wide range of furans and Grignard reagents and low yields have been found only in the reactions with the benzylic and allylic reagents which are delocalized anions. A mechanistic interpretation is given.

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