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Base-Catalyzed Dehalogenation of 2,6-Di-tert-butyl-4-iodophenol Formation and Structure of a New Oxocyclohexadienylidene Bisphenol

✍ Scribed by Reischl, Gerald ;Rieker, Anton ;Maichle-Mössmer, Cäcilia ;Abram, Sonja

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 419 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619960718

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✦ Synopsis

Abstract

2,6‐Di‐tert‐butyl‐4‐iodophenol (1) does not react to the keto carbene 4 under strongly basic conditions and exclusion of oxygen, in contrast to a report in the literature. In the presence of oxygen, however, oxidation takes place. Reaction times and product pattern strongly depend on the concentration of O~2~. Besides biphenyl 2, diphenoquinone 3, and quinone 5, a new (oxocyclohexadienylidene)bisphenol 6 was isolated, and its molecular structure was determined by X‐ray crystallography. A radical mechanism is suggested for the formation of the above products from 1. The bisphenol 6 was also synthesized by thermolysis of the quinone diazide 11 in the presence of 3.

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