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

doi:10.1021/acs.joc.1c03160

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 journal › Article › peer-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 language	English
Pages (from-to)	4692-4701
Number of pages	10
Journal	The Journal of Organic Chemistry
Volume	87
Issue number	7
Early online date	14 Mar 2022
DOIs	https://doi.org/10.1021/acs.joc.1c03160
Publication status	Published - 13 Apr 2022

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Copyright © 2022 The Authors / American Chemical Society. Open Access. This work is distributed under the Creative Commons Attribution 4.0 License.
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title = "Access to diarylmethanols by Wittig rearrangement of ortho-, meta- and para-benzyloxy-N-butylbenzamides",

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.",

author = "Aitken, \{R Alan\} and Harper, \{Andrew D.\} and Inwood, \{Ryan A.\} and Slawin, \{Alexandra M. Z.\}",

note = "Authors 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. ",

year = "2022",

month = apr,

day = "13",

doi = "10.1021/acs.joc.1c03160",

language = "English",

volume = "87",

pages = "4692--4701",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "7",

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TY - JOUR

T1 - Access to diarylmethanols by Wittig rearrangement of ortho-, meta- and para-benzyloxy-N-butylbenzamides

AU - Aitken, R Alan

AU - Harper, Andrew D.

AU - Inwood, Ryan A.

AU - Slawin, Alexandra M. Z.

N1 - Authors 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.

PY - 2022/4/13

Y1 - 2022/4/13

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85127214499

U2 - 10.1021/acs.joc.1c03160

DO - 10.1021/acs.joc.1c03160

M3 - Article

SN - 0022-3263

VL - 87

SP - 4692

EP - 4701

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 7

ER -

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

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CRITICAT CDT: Critical Resource Catalysis - CRITICAT

CCDC 2105490 - 2105493: Experimental Crystal Structure Determination

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

Abstract

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CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Datasets

CCDC 2105490 - 2105493: Experimental Crystal Structure Determination

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