A non-concerted single-electron transfer pathway has been established for the reductive elimination of α-iodo epoxides to allylic alcohols with sodium naphthalide; the exchange reaction between BuLi and RI must proceed exclusively by single-electron transfer to account for identity of rates of reaction between BuLi and epimeric 3-iodo-4β,5β-epoxycholestanes.
S. K. Pradhan and M. Girijavallabhan, J. Chem. Soc., Chem. Commun., 1975, 591 DOI: 10.1039/C39750000591
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