Electrophilic fluorination of organic compounds

Details Electrophilic fluorination of organic compounds Electrophilic fluorination of organic compounds

C - Chemistry, Metallurgy

07

C

260/650, 260/7,

C07C 23/20 (2006.01) C07B 39/00 (2006.01) C07C 17/10 (2006.01) C07J 1/00 (2006.01) C07J 5/00 (2006.01) C07J 7/00 (2006.01) C07J 9/00 (2006.01) C07J 41/00 (2006.01) C07J 53/00 (2006.01) C07J 71/00 (2006.01)

Patent

CA 1064475

ABSTRACT OF THE DISCLOSURE Saturated organic compounds containing a hydrogen atom bound to a tertiary carbon atom may be electrophilically fluorinated by reacti?n with an electrophilic fluorinating agent such as molecular fluorine or trifluoromethyl hypofluorite under conditions whereby the formation of free fluorine radicals is suppressed, e.g. by the presence of a free radical inhibitor such as oxygen or nitrobenzene, the reactants being substantially homogeneously dispersed in a liquid medium, e.g. A solvent medium such as fluorotrichloro- methane or chloroform/fluorotrichloromethane. so that the said hydrogen atom is electrophilically replaced by a fluorine atom. The fluoroination is highly selective and, in the case of complex substrates such as saturated steroids which contain a ?umber of tertiary - 1a - C-H bonds, may be substantially completely confined to replacement of the hydrogen atom at the tertiary carbon atom which has the highest electron density about the C-H bond. The electron density and thus the direction of the fluorination may be controlled by appropriate selection of substituent groupings in the substrate molecule. Novel 14.alpha.-fluorosteroids are also disclosed, including compounds having valuable androgenic or progestational activity and useful synthetic inter- mediates. - 1b -

228313

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