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6921551 
Journal Article 
Direct trifluoro-methoxylation of aromatics with perfluoro-methyl-hypofluorite 
Venturini, F; Navarrini, W; Famulari, A; Sansotera, M; Dardani, P; Tortelli, V; , 
2012 
Yes 
Journal of Fluorine Chemistry
ISSN: 0022-1139
EISSN: 1873-3328 
ELSEVIER SCIENCE SA 
LAUSANNE 
140 
43-48 
English 
WOS:000306866000006 
The reactivity of CF3OF (FM) has been widely studied especially in halogenated olefinic systems and its use in pharmaceutical synthesis as a mild radical and electrophilic fluorinating agent is well documented. On the other hand, the chemical behavior of the perfluoro-methyl-hypofluorite with aromatic substrates is much less studied. Up to now few and scattered data regarding its use as electrophilic fluorinating agent of variously substituted aromatic compounds are found in the literature. In this work the reactivity of CF3OF with simple electron rich and electron poor aromatics (alpha,alpha,alpha-trifluoro-toluene, toluene. benzene, chloro-benzene, methoxybenzene) has been investigated. The possibility of selectively bind the trifluoro-methoxy group (via radical mechanism) or the fluorine atom (via electrophilic addition) by varying the reaction conditions has been explored. In particular we have observed that the trifluoromethoxy free radical substitution can be the main synthetic pathway if the reaction is promoted by an independent and steady source of CF3O radical. (C) 2012 Elsevier B.V. All rights reserved.