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Acid-catalyzed reaction of 2,6-di-T-butyl-4-hydroperoxy-2,5-cyclohexadienones and their acetates

✍ Scribed by A. Nishinaga; K. Nakamura; T. Matsuura; A. Rieker; D. Koch

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
235 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

Highly regioselective oxygenation products from 2,6-di-t-butylphenols display interesting chemical behavior under strongly basic conditions, being efficiently utilized for synthesis of hydroquinones, 1 o-benzoquinones, 2 cyclopentadienones, 3 3-hydroxyphenylacetic acids,' cyclopentenones, 5 and B-quinoxyacetic acids. 6 These investigations have revealed the chemical reactivity of E-quinolate a (A) and E-quinoxy radical (I&): 1 readily undergoes ketoni-

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In a previous paper,' we reported a novel base-catalyzed rearrangement of R-peroxyquinol esters derived from 2,6-di-t-butylphenols leading to quinoxyacetic acid derivatives, where the peroxy bond cleaves even below -60 "C. Nature of the peroxy bond cleavage has been remained n