ChemInform Abstract: Reactivity of a 10-I-3 Hypervalent Iodine Trifluoromethylation Reagent with Phenols

Autor:	Raffael Koller, Antonio Togni, Kyrill Stanek
Rok vydání:	2009
Předmět:	chemistry.chemical_compound Electrophilic substitution Deprotonation chemistry Trifluoromethylation Reagent Electrophile Hypervalent molecule Reactivity (chemistry) General Medicine Benzene Medicinal chemistry
Zdroj:	ChemInform. 40
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200908089
Popis:	The reaction of the 10-I-3 hypervalent iodine electrophilic trifluoromethylation reagent 1-trifluoromethyl-1,2-benziodoxol-3-(1H)-one (2) with 2,4,6-trimethylphenol, after deprotonation with NaH and in the presence of 18-crown-6 in a polar, nonprotic solvent, affords 1,3,5-trimethyl-2-(trifluoromethoxy)benzene (4) only as a byproduct. Trifluoromethylation occurs preferentially at the ortho- and para-positions of the aromatic core, giving the corresponding trifluoromethylcyclohexadienones 5 and 6. In case the ortho- and/or para-positions are not substituted, the corresponding products of an aromatic, electrophilic substitution are obtained in moderate yield, for example, 2-trifluoromethyl-4-tert-butylphenol (10a) from 4-tert-butylphenol (10).
Databáze:	OpenAIRE
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