ORGN 59

Radical cyclization reactions have become increasingly important in synthetic organic chemistry, although the necessary use of the Bu₃SnH/AIBN system prohibits their use for many applications. Consequently, many efforts have been made to find safer and easily removable reagents for radical reactions. For instance, Et₃B/O₂ is used as a radical initiator and several phosphorus reagents are known hydrogen atom sources. This study uses 1-ethylpiperidine hypophosphite (EPHP) with vinylborane 1 to effect the radical cyclization, producing cyclopentanemethanol after oxidation with NaOH and H₂O₂. This method is nontoxic and provides easy separability. Ongoing studies will investigate the scope of this methodology, including the use of the remaining boron after cyclization in providing further transformations.