Gem-disubstituted cyclohexadienones and their production

Details Gem-disubstituted cyclohexadienones and their production Gem-disubstituted cyclohexadienones and their production

1988-04-04

1989-02-14

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

556418, 544229, 549215, C07F 718, C07F 710

Patent

active

048047724

ABSTRACT:
Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts devoid of fluorine (e.g., LiN.sub.3, NaN.sub.3, KN.sub.3, NaCN KCN, CsCN, NaOH, KOH, K.sub.2 CO.sub.3, and Cs.sub.2 CO.sub.3). The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.

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Fujita et al., J. Am. Chem. Soc., 1985, 107, 4085-4087.

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