What a difference the solvent makes! Unlike in conventional solvents, nonstrained ketones such as cyclohexanone react smoothly with hydrogen peroxide in 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) to give lactones. The reaction proceeds via an isolatable spiro‐bisperoxide, which undergoes a highly exothermic acid‐catalyzed rearrangement to two equivalents of lactone (see Equation and IR thermogram).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.