Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy‑N‑Butylbenzamides

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 wi...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-04, Vol.87 (7), p.4692-4701
Main Authors: Aitken, R. Alan, Harper, Andrew D, Inwood, Ryan A, Slawin, Alexandra M. Z
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c03160