Organic compounds of fluorine. XII. The synthesis of 2-carboxy-3-methyl-5-fluorovaleric acid, 2-carboxy-5-fluorocaproic acid, and 2-carboxy-5, 5-difluorocaproic …
M Hudlický, B Kakáč, I Lejhancová
Index: Hudlicky,M. et al. Collection of Czechoslovak Chemical Communications, 1967 , vol. 32, p. 183 - 189
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Abstract
Similarly, l-bromo-3-fluorobutane1 or l-iodo-3-fluorobutane1 and diethyl malonate yielded ethyl 2-ethoxycarbonyl-5-fluorocaproate (lIla) which was hydrolyzed to 2-carboxy-5- fluorocaproic acid (IIlb). Its structure was proved by oxidation to succinic acid. In an attempt to decarboxylate the acid IlIb hydrogen fluoride was eliminated almost quantitatively and a fluorine-free product, probably o-caprolactone, was obtained instead of the expected 5- ...
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