BETA-NITROGENATED RADICALS IN ORGANIC-SYNTHESIS - REACTIONS WITH ELECTROPHILIC OLEFINS

The reaction of iodoamide 1a or iodocarbamates 1b,c with electrophilic olefins 2a-e and in situ generated tributyltin hydride (from tributyl tin chloride,in a substoichiometric amout and an excess of sodium boro hydride) in the presence of a catalytic amount of AIBN in dry ethanol at 0 to 20 degrees C yields, after treatment with aqueous sodium fluor ide, the expected coupling products 3aa-ce in moderate yields. Compoun ds 4a-c resulting from an iodine/hydrogen exchange in the starting mat erials 1a-c are also obtained as by-products in variable amounts.