SYNTHESES WITH F-ALKYL RADICALS FROM F-ALKYL IODIDES - AMINE AND AMINE SALT INDUCED ADDITION TO ALKENES

Free radical induced reactions of 1-iodo-F-alkanes (RFI) with diallyl ether, N-methyldiallylamine, and 1-hep-tene, using an amine or amine salt as initiator at 120-140°C, are described. Copper(I) or copper(II) ions appear to inhibit the reaction, while copper ion and an amine or amine salt in no case gave faster reaction than amine or amine salt alone. These results are contrasted with CCl4additions which are strongly accelerated by this initiating system. The best initiator found for RFI addition was benzyltriethylammonium chloride, which gave 94% conversion of diallyl ether to adducts at 135°C in 3 h. An azonitrile initiator would be preferred, however, for most RFI additions which can be carried out at 50-110°C. Copyright © 1979, American Chemical Society. All rights reserved.