Access to diarylmethanols by Wittig rearrangement of ortho-, meta- and para-benzyloxy-N-butylbenzamides
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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.
Aitken , R A , Harper , A D , Inwood , R A & Slawin , A M Z 2022 , ' Access to diarylmethanols by Wittig rearrangement of ortho -, meta - and para -benzyloxy- N -butylbenzamides ' , The Journal of Organic Chemistry , vol. 87 , no. 7 , pp. 4692-4701 . https://doi.org/10.1021/acs.joc.1c03160
The Journal of Organic Chemistry
Copyright © 2022 The Authors / American Chemical Society. Open Access. This work is distributed under the Creative Commons Attribution 4.0 License.
DescriptionAuthors thank EPSRC (UK) for a DTA studentship to ADH (Grant EP/L505079/1), EPSRC (UK) and CRITICAT Centre for Doctoral Training for a studentship to RAI (Grant code: EP/L016419/1) and the EPSRC UK National Mass Spectrometry Facility at Swansea University.
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