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

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

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 concentrati...

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Veröffentlicht in:Liebigs Annalen 1996-07, Vol.1996 (7), p.1183-1186
Hauptverfasser: Reischl, Gerald, Rieker, Anton, Maichle-Mössmer, Cäcilia, Abram, Sonja
Format: Artikel
Sprache:eng
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1,4‐Keto carbene
4-Keto carbene
Bisphenol
Diphenoquinone
Phenol oxidation
Phenoxy radical
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container_end_page 1186
container_issue 7
container_start_page 1183
container_title Liebigs Annalen
container_volume 1996
creator Reischl, Gerald
Rieker, Anton
Maichle-Mössmer, Cäcilia
Abram, Sonja
description 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 O2. 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.
doi_str_mv 10.1002/jlac.199619960718
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source Wiley Online Library Journals Frontfile Complete
subjects 1,4‐Keto carbene
4-Keto carbene
Bisphenol
Diphenoquinone
Phenol oxidation
Phenoxy radical
title Base-Catalyzed Dehalogenation of 2,6-Di-tert-butyl-4-iodophenol Formation and Structure of a New Oxocyclohexadienylidene Bisphenol
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