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The reagent, ArSeCN-M(OTf) n , is prepared from equimolar amounts of an aromatic selenocyanate and metal trifluoromethanesulfonate. It reacts with unsaturated alcohols and carboxylic acids to give cyclic ethers and lactones, respectively.Depending on conditions, reactions of trans-2allylcyclohexanol with the reagent selectively afford exo-cyclized tetrahydrofuran or endo-cyclized tetrahydropyran.The mechanism of exo/endo selection is discussed based on molecular dynamics studies.
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Murata et al. (2000) studied this question.
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