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The mechanism of the gibbs reaction. Part 2: The ortho ⇉ ortho 2,4-cyclohexadiene-1-one rearrangement of the reaction product of 2,6-di-tert-butyl-4-chlorophenol and 2,6-dichlorobenzoquinone N-chloroimine

✍ Scribed by István Pallagi; András Toró; József Müller

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
346 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

The saturation transfers which were observed during the 'H NOE difference measurements prove an orrho + ortho 2,4-cyclohexadiene-l-one rearrangement of the reaction product of 2,6-di-fert-butyl-4-chlorophenol and 2,6dichlorobenzoquinone N-chloroimine. This process is an intramolecular rearrangement.

In 1927 H. D. Gibbs suggested the use of 2,6-dibromobenzoquinone N-chloroimine (la) as a phenol assay reagent2 (Scheme 1). According to his method, phenol (2a) reacts quantitatively with N-chloroimine la in 7.

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