Journal of Fluorine Chemistry p. 19 - 40 (1988)
Update date:2022-07-29
Topics:
Naji, Naima
Moreau, Patrice
The present paper deals with a systematic study of the reaction of organometallic compounds, especially Grignard and lithium reagents, upon hemifluorinated ketones R-CO-RF. Whereas organolithium reagents lead, as in hydrocarbon series, to the exclusive formation of tertiary alcohols, by addition, Grignard reagents give a very high percentage of secondary alcohols by reduction. These results are initially explained by the differences in the reaction mechanisms of the organometallics : an ionic reaction for the lithium derivatives, and a cyclic concerted mechanism, involving reactions sensitive to substituent effects, for Grignard reagents. In these latter cases, the reduction alcohol percentage, which is already high for the short RF derivatives, increases with increasing length of the F-alkyl chain. A discussion is presented in order to explain this result, by considering the influence of both electronic and steric effects of F-alkyl groups. The results we obtained, compared to those of the literature, lead us to confirm the particular role of perfluorinated groups CnF2n+1 on the behaviour of the molecules in which they are substituted.
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