Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate: crystal structure of the product

F. Richmond Hewgill; David G. Hewitt; Graeme B. Howie; Colin L. Raston; Rauleigh J. Webb; Allan H. White

doi:10.1039/P19790000290

Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate: crystal structure of the product

F. Richmond Hewgill, David G. Hewitt, Graeme B. Howie, Colin L. Raston, Rauleigh J. Webb, Allan H. White

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The major product of the reaction, previously described as an acetoxybenzoxet, is now shown to be 4,10a-dihydro-7-methoxy-4-oxo-2,9-di-t- butyloxepino[2,3-b]benzofuran-10a-yl acetate (4). This assignment is based on X-ray cristallographic analysis of the corresponding benzoate. The biphenyl system is re-formed on reduction of the acetate, and reaction with acid converts the acetate into benzofuran-3(2H)-one derivatives.

Original language	English
Pages (from-to)	290-298
Number of pages	9
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	0
DOIs	https://doi.org/10.1039/P19790000290
Publication status	Published - 1979
Externally published	Yes

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Hewgill, F. R., Hewitt, D. G., Howie, G. B., Raston, C. L., Webb, R. J., & White, A. H. (1979). Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate: crystal structure of the product. Journal of the Chemical Society, Perkin Transactions 1, (0), 290-298. https://doi.org/10.1039/P19790000290

@article{bf49e900eb1740859be56cdaf72e8417,

title = "Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate: crystal structure of the product",

abstract = "The major product of the reaction, previously described as an acetoxybenzoxet, is now shown to be 4,10a-dihydro-7-methoxy-4-oxo-2,9-di-t- butyloxepino[2,3-b]benzofuran-10a-yl acetate (4). This assignment is based on X-ray cristallographic analysis of the corresponding benzoate. The biphenyl system is re-formed on reduction of the acetate, and reaction with acid converts the acetate into benzofuran-3(2H)-one derivatives.",

author = "Hewgill, {F. Richmond} and Hewitt, {David G.} and Howie, {Graeme B.} and Raston, {Colin L.} and Webb, {Rauleigh J.} and White, {Allan H.}",

year = "1979",

doi = "10.1039/P19790000290",

language = "English",

pages = "290--298",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "0",

}

Hewgill, FR, Hewitt, DG, Howie, GB, Raston, CL, Webb, RJ & White, AH 1979, 'Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate: crystal structure of the product', Journal of the Chemical Society, Perkin Transactions 1, no. 0, pp. 290-298. https://doi.org/10.1039/P19790000290

Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate: crystal structure of the product. / Hewgill, F. Richmond; Hewitt, David G.; Howie, Graeme B. et al.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 0, 1979, p. 290-298.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate

T2 - crystal structure of the product

AU - Hewgill, F. Richmond

AU - Hewitt, David G.

AU - Howie, Graeme B.

AU - Raston, Colin L.

AU - Webb, Rauleigh J.

AU - White, Allan H.

PY - 1979

Y1 - 1979

N2 - The major product of the reaction, previously described as an acetoxybenzoxet, is now shown to be 4,10a-dihydro-7-methoxy-4-oxo-2,9-di-t- butyloxepino[2,3-b]benzofuran-10a-yl acetate (4). This assignment is based on X-ray cristallographic analysis of the corresponding benzoate. The biphenyl system is re-formed on reduction of the acetate, and reaction with acid converts the acetate into benzofuran-3(2H)-one derivatives.

AB - The major product of the reaction, previously described as an acetoxybenzoxet, is now shown to be 4,10a-dihydro-7-methoxy-4-oxo-2,9-di-t- butyloxepino[2,3-b]benzofuran-10a-yl acetate (4). This assignment is based on X-ray cristallographic analysis of the corresponding benzoate. The biphenyl system is re-formed on reduction of the acetate, and reaction with acid converts the acetate into benzofuran-3(2H)-one derivatives.

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U2 - 10.1039/P19790000290

DO - 10.1039/P19790000290

M3 - Article

AN - SCOPUS:37049107919

SN - 1472-7781

SP - 290

EP - 298

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 0

ER -

Oxidation of alkoxyphenols. Part 23. A re-examination of the reaction of 5,5′-dimethoxy-3,3′-di-t-butylbiphenyl-2,2′-diol with lead tetraacetate: crystal structure of the product

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