Nucleophilic Displacement Reactions of Halogenated Cyclobutenes¹

Fluorination of fluoro-cyclobutene with high-valency metal fluoride

“…3,3,4,4-Tetrafluorocyclobutene was prepared by dehydrochlorination of 1-chloro-2,2,3,3-tetrafluorocyclobutane [17], which was prepared by cross-coupling cyclobutanation of tetrafluoroethylene and vinyl chloride [12].…”

Organic Fluorine Chemistry

“…The following examples are illustrative [403,404]: (232) C F 2-CH 1 KOH, EtOH ... C F 2-C H 1 KOH, EtOH~ CF2-CH [403] I II From the enormous experimental data, especially in the field of cyclic polyfluorohalo-olefins, the following rules can be derived to help estimate the probable results of a reaction [405]:…”

Polyfluoroalkyl ethers of alicyclic fluoroolefins

“…The carbon and hydrogen analyses were made by Galbraith Laboratories, Inc., Knoxville, Tenn. The GLPC data were obtained from (A) a column % inch by 15 feet, packed with 30% Carbowax 20M on Chromosorb W, or (B) a column Vie inch by 12 feet, packed with 20% Carbowax 20M on Gas Chrom Q. Ethyl piñonate, IB, 360 grams (1.65 mole) 1.4526 [lit. 1.4526 (4)], prepared by the esterification of cis-dl-pinonic acid with ethanol in toluene using p-toluenesulfonic acid as a catalyst, was reduced with lithium aluminum hydride…”

“…The fluid characteristics of these two types of ethers are compared, including the effects of ring size.IN UCLEOPHILIC displacement of halogens in alicydic perhalo-olefins by alkoxide ions yields two types of ethers, depending upon the nature of the vinylic halogen in the olefin. Most of the reported work (6,7,8,10,11,12,14,15) relates to the reactions of the perhalocyclobutene…”