Abstract
Abstract Perfluoro-2-methyl-2-pentene (PMP) reacts with carboxylic acids, alcohols, and 2-pyridone, giving Michaeltype addition products, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3-acyloxypentane, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3-alkoxypentane, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3 (2-pyridyloxy)pentane, respectively, in good yields. In the presence of bases, carboxylic acids give acid fluorides, 1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-3-pentanone, and 1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-3-acyloxy-2-pentene (4), the yields changing with base, solvent, phase-transfer catalyst, and their combination. In the presence of triethylamine, fluorination occurs exclusively, producing acid fluorides in good yields. Alcohols and 2-pyridone are converted into alkyl fluorides and 2-fluoropyridine, respectively, with use of triethylamine as a base with an aprotic solvent. The reactions of PMP with 4-pyridone and 6-chloro-2-ethyl-5-methyl-4(3H)-pyrimidone were also examined. The fluorination reactions were rationalized by preferential replacement of the vinylic fluorine of PMP and a good leaving function of the perfluoro enol group of the intermediates such as 4.
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