CYCLIZATION OF ETHYL DIALLYLACETATE OR ETHYL DIALLYLMALONATE TO CYCLOPENTANE DERIVATIVES DURING ADDITION OF PERFLUOROALKYL AND TRICHLOROMETHYL RADICALS

Radical cyclization reactions of 4-substituted 1,6-heptadienes were studied. Five- but not six-membered rings were obtained from iodoperfluoroalkanes or carbon tetrachloride with ethyl diallylacetate (I) or with ethyl diallylmalonate (II). Various derivatives of the cyclic adducts were prepared which confirmed the structures suggested by spectroscopic and other evidence. These reactions provide an entry into the area of partially fluorinated alicyclic carboxylic acids. Free-radical reaction of I with a variety of thiols or with diethyl phosphite is reported to have given five- and six-membered ring products; cyclopolymerization of II also is supposed to lead to six-membered ring structures. © 1969, American Chemical Society. All rights reserved.