Iodine Atom Transfer Addition Reactions with Alkynes. Part 1. Alkyl Iodides.

Abstract Simple 2° - and 3° -alkyl iodides add smoothly to electron deficient alkynes under standard atom transfer conditions 10% Bu 3 SnSnBu 3 , sunlamp photolysis. Mechanistic experiments help to interpret stereochemical and yield trends, and a new model for atom abstraction reactions of rapidly inverting a-vinyl radicals is proposed.