Hayashi rearrangement

Hayashi rearrangement

The Hayashi rearrangement is the chemical reaction of ortho-benzoylbenzoic acids catalyzed by sulfuric acid or phosphorus pentoxide. [cite journal
title = A new isomerism of halogenohydroxybenzoyltoluic acids
author = Mosuke Hayashi
journal = Journal of the Chemical Society
volume =
issue =
pages = 2516
year = 1927
url =
doi = 10.1039/JR9270002516
] [ cite journal
title = A new isomerism of halogenohydroxybenzoyltoluic acids. Part II. 2-(5-Chloro-2-hydroxybenzoyl)-5(4?)-methylbenzoic acid
author = Mosuke Hayashi
journal = Journal of the Chemical Society
volume =
issue =
pages = 1513
year = 1930
url =
doi = 10.1039/JR9300001513
; p. 1520 DOI|10.1039/JR9300001520; p. 1524DOI|10.1039/JR9300001524
]

This reaction proceeds through electrophilic acylium ion attack with a spiro intermediate ["The Hayashi Rearrangement of Substituted o-Benzoylbenzoic Acids" Reuben B. Sandin, Russell Melby, Robert Crawford, and Donald McGreer J. Am. Chem. Soc. 1956 pp 3817 - 3819; DOI|10.1021/ja01596a069] ["Name Reactions: A Collection of Detailed Reaction Mechanisms" By Jie Jack Li Published 2003 Springer ISBN 3540402039]

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