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

[Image: see text] 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 metho...

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Autores principales: Aitken, R. Alan, Harper, Andrew D., Inwood, Ryan A., Slawin, Alexandra M. Z.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9007461/
https://www.ncbi.nlm.nih.gov/pubmed/35286089
http://dx.doi.org/10.1021/acs.joc.1c03160
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author Aitken, R. Alan
Harper, Andrew D.
Inwood, Ryan A.
Slawin, Alexandra M. Z.
author_facet Aitken, R. Alan
Harper, Andrew D.
Inwood, Ryan A.
Slawin, Alexandra M. Z.
author_sort Aitken, R. Alan
collection PubMed
description [Image: see text] 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.
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spelling pubmed-90074612022-04-14 Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides Aitken, R. Alan Harper, Andrew D. Inwood, Ryan A. Slawin, Alexandra M. Z. J Org Chem [Image: see text] 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. American Chemical Society 2022-03-14 2022-04-01 /pmc/articles/PMC9007461/ /pubmed/35286089 http://dx.doi.org/10.1021/acs.joc.1c03160 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Aitken, R. Alan
Harper, Andrew D.
Inwood, Ryan A.
Slawin, Alexandra M. Z.
Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides
title Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides
title_full Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides
title_fullStr Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides
title_full_unstemmed Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides
title_short Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides
title_sort access to diarylmethanols by wittig rearrangement of ortho-, meta-, and para-benzyloxy-n-butylbenzamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9007461/
https://www.ncbi.nlm.nih.gov/pubmed/35286089
http://dx.doi.org/10.1021/acs.joc.1c03160
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