Radical addition reaction of bis(naphth-1,8-diyl-8-oxy)hydrophosphorane to olefins

In the presence of 1,1′‐azobis(cyclohexanecarbonitrile) (ACHCN), the reaction of bis(naphth‐1,8‐diyl‐8‐oxy)hydrophosphorane with an equimolar amount of terminal and internal olefins gave the corresponding alkylphosphoranes. In the reactions with styrene and methyl acrylate, 2:1 olefin–hydrophosphorane adducts were obtained as a minor product. The reactions with terminal olefins were entirely regioselective and more efficient than those with internal olefins. In the absence of ACHCN, the radical addition reaction of the hydrophosphorane to terminal and internal olefins could also proceed slowly. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:538–544, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20719