Terminal and internal alkynes react with I2 or KI and nitrates in acetic acid under mild conditions to give the corresponding 1-iodo-2-nitroalkenes as the major products. The effect of the reactant nature and reaction conditions on the yield of products was studied. Oxygen was found to play an important role in the formation of the target products. A possible mechanism of the reaction includes a series of redox transformations of I2 or I- and NO- 3 to form INO2 which then adds to alkynes by a radical path. In reactions with potassium iodide, oxygen acts as an additional oxidant which converts NO into active nitrogen dioxide.
|Журнал||Russian Journal of Organic Chemistry|
|Состояние||Опубликовано - сен 1999|
ASJC Scopus subject areas
- Organic Chemistry