RELATIVE RATES OF ADDITION OF IODINE ISOCYANATE TO UNSATURATED COMPOUNDS

The relative rates of addition of iodine isocyanate (generated in situ from iodine and silver cyanate) to unsaturated compounds was studied with 18 unsaturated compounds at a temperature range from —80 to 3°, over a range of concentrations, and at various ratios of reactants. Rates of reaction decrease with decreasing temperature and concentration of unsaturated compound and also when excess olefin is used. Vinyl and isopropenyl acetates react very rapidly whereas alkynes react slowly. When an electron-withdrawing carbonyl group or chlorine atom is attached to the double bond, essentially no reaction occurs. The relative rates of addition of in situ generated iodine isocyanate to unsaturated compounds follows a series typical of an electrophilic reaction. © 1968, American Chemical Society. All rights reserved.