All articles of this category Tetrahydrofuran is readily cleaved by tert -butyldimethylsilyl iodide generated in situ by reaction of the chloride with sodium iodide in acetonitrile to give the corresponding 1-silyloxy-4-iodobutane, which in turn undergoes a number of useful functionalizations of the iodo group including substitutions with hetero nucleophiles, such as amine, thiolate, sulfinate, and phosphite and carbon nucloephiles such as enolate and acetylide, with survival of the silyloxy group.
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Nyström et al. (1988) studied this question.