In:
Canadian Journal of Chemistry, Canadian Science Publishing, Vol. 64, No. 1 ( 1986-01-01), p. 138-141
Kurzfassung:
Replacement of a carboxyl function by fluorine, fluorodecarboxylation, is a new process that can be accomplished by the reaction of alkanoic acids with xenon difluoride. Primary, tertiary, and benzylic acids perform best in the reaction, which is conducted at room temperature in methylene chloride or chloroform solution. A reaction mechanism is proposed in which the acid is initially converted to a fluoroxenon ester, RCO 2 XeF. The esters of the primary and secondary acids react by nucleophilic displacement by fluoride, as evidenced by incorporation of 18 F − and no reactions common to free radicals or carbocations. The esters of the tertiary and benzylic acids react by converting to free radicals that can be further oxidized to carbocations. Thus incorporation of 18 F − and racemization are observed with α-methoxy-α-trifluoromethylphenylacetic acid. Hydroxyl and amino functions inhibit the reaction. Aromatic and vinylic acids do not react.
Materialart:
Online-Ressource
ISSN:
0008-4042
,
1480-3291
Sprache:
Englisch
Verlag:
Canadian Science Publishing
Publikationsdatum:
1986
ZDB Id:
1482256-8
