The synthesis of 10-17 membered 4-oxolactones 2 from alkyl iodides 1 h
aving an acryloxy moiety at the termini, carbon monoxide, and TTMSS (o
r tin hydride) takes place cleanly in moderate to good yield under fre
e radical conditions. Low concentrations of 1 (0.005-0.01 M) are favor
able for both intermolecular trap of CO and intramolecular acyl radica
l addition to the C-C double bond,