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Base‐Catalyzed Dehalogenation of 2,6‐Di‐ tert ‐butyl‐4‐iodophenol Formation and Structure of a New Oxocyclohexadienylidene Bisphenol
Author(s) -
Reischl Gerald,
Rieker Anton,
MaichleMössmer Cäcilia,
Abram Sonja
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960718
Subject(s) - chemistry , biphenyl , halogenation , catalysis , thermal decomposition , carbene , bisphenol a , bisphenol , oxygen , medicinal chemistry , decomposition , quinone , polymer chemistry , photochemistry , organic chemistry , epoxy
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 .