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Chlorocyanoacetylene and Cyanoacetylene.-The pyrolysis apparatus was the same as that used for the copyrolysis of acetonitrile and carbon tetrachloride, with a slight modification.13The whole system was evacuated with an aspirator while the sample was fed by the leak method. The reaction product, most of which condensed as a crystalline mass in the first trapping tube, was dissolved in tetrachloroethylene and analyzed by gas chromatography. The column was SE-30 (10%) or TCP (10%) on Chromosorb W. The temperature of the column was 65°. Typical results are shown in Table I.Malononitrile. General Procedure.-Four grams of chlorocyanoacetylene was dissolved in a solvent and the solution was placed in a four-necked flask equipped with a thermometer, an inlet tube for ammonia, a reflux condenser, and a mechanical stirrer. With efficient stirring, a stream of gaseous ammonia was introduced directly into this solution. The rate of feeding ammonia was ca. 100 ml/min, which corresponded to the rate of consumption of ca. 0.2 g of chlorocyanoacetylene/min. When the inside temperature reached 30°, cooling was started in order to maintain this temperature during the reaction period. After ammonia had been introduced into the reaction mixture for 20 min, the precipitated NH

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and C4F9IF2 and confirmed many of the observations reported herein. I want to express particular appreciation to Walter G. Barber for his assistance throughout this work. His intrepid handling of C1FS demonstrated that even the most dangerous work can be performed safely. Mr. Barber also built the fluo-3061 rine-handling equipment, with assistance and advice from Edward Hancock, our resourceful mechanic.Thomas E. Beukelman performed the nmr studies, and I owe a great deal to his imaginative examination of the spectra. Dr. James Proctor conducted the X-ray study of solid Ci0F2iIF2.Fluorocyclopropanes. III. 1,4-Cycloaddition Reactions of Perfluorocyclopropene and 1,2-Bis (trifluoromethyl) -3,3-difluorocyclopropene

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Perfluorocyclopropene undergoes free‐radical copolymerization with ethylene, isobutylene, cis‐ and trans‐2‐butene, vinyl acetate, methyl vinyl ether, vinyl chloride, styrene, acrylonitrile, tetrafluoroethylene, vinyl fluoride, and vinylidene fluoride. The copolymerization proceeds most readily with electron‐rich olefins such as methyl vinyl ether (to yield a 1:1 copolymer), but conditions were found to give copolymers with electron‐deficient olefins such as tetrafluoroethylene and vinylidene fluoride. Copolymers with methyl vinyl ether, tetrafluoroethylene, vinyl fluoride, and vinylidene fluoride were examined in detail. Evidence is presented that the perfluorocycloproply ring is incorporated intact into the copolymer and can be subsequently isomerized to a perfluoropropenyl unit by heating at 200–300°C.

Hexafluor‐propylenoxid (I) liefert beim Erhitzen das Difluor‐carben (II), das mit Olefinen (III) zu den Difluorcyclopropanen (IV) führt.