Access to diarylmethanols by Wittig rearrangement of ortho-, meta- and para-benzyloxy-N-butylbenzamides

R Alan Aitken*, Andrew D. Harper, Ryan A. Inwood, Alexandra M. Z. Slawin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically-pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.
Original languageEnglish
Pages (from-to)4692-4701
Number of pages10
JournalThe Journal of Organic Chemistry
Volume87
Issue number7
Early online date14 Mar 2022
DOIs
Publication statusPublished - 13 Apr 2022

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