M. Modena

Addition of carbon tetrachloride to 3,3,4,4-tetrafluorohexa-1,5-diene

The free-radical reaction of carbon tetrachloride with 3,3,4,4-tetrafluoro-1,5-hexadiene is described. Initiation of the chain process by a variety of redox-transfer systems has been studied. The cyclic isomeric monoadducts have been shown to possess four-, five-, six-, and seven-membered ring structures. The extent of rearrangement observed in the products is greatly influenced by metallic salt additives and by the solvent. However, the solvent effect is not observed in the presence of some copper(II) species.

Novel method of producing radicals of the hex-5-enyl type

Addition to alk-1-enes or alk-1-ynes of the radical obtained from 3,3,4,4-tetrafluoro-4-iodobut-1-ene by either peroxide or metal-salt initiation, provides a convenient route to hex-5-enyl radicals. The size of the rings produced from these radicals is discussed on the basis of the polarisation of the terminal double bond and of the nature of the attacking radical.

The peroxide-initiated addition of 1,1-dibromotetrafluoroethane to ethylene, propene, and 2-methylpropene

1,1-Dibromotetrafluoroethane has been found to give simple addition products with ethylene, propene, and 2-methylpropene in the presence of di-t-butyl peroxide. The products of dehydrohalogenation of the adducts are described and their structures elucidated by spectroscopic methods.