Japanese Patent JPS514102

A

Saturated organic compounds containing a hydrogen atom bound to a tertiary carbon atom may be electrophilically fluorinated by reaction 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 fluorotrichloromethane or chloroform/fluorotrichloromethane, so that the said hydrogen atom is electrophilically replaced by a fluorine atom. The fluorination is highly selective and, in the case of complex substrates such as saturated steroids which contain a number of tertiary 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 intermediates.

DEIRETSUKU HARORUDO RICHAADO B
ROBAATO HENRII HETSUSE

JP6695975A

January 14, 1976

June 03, 1975

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RES INST MEDICINE CHEM

C07B31/00; C07B39/00; C07C17/00; C07C17/10; C07C19/08; C07C19/10; C07C19/12; C07C23/20; C07C67/00; C07J1/00; C07J5/00; C07J7/00; C07J9/00; C07J41/00; C07J53/00; C07J75/00; (IPC1-7): C07B9/00; C07C23/20; C07J1/00

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