Ring closure reaction of 4-tert-butyl-4-penten-1-ol and 4-tert-butyl-1-pentanol with lead tetraacetate
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The lead tetraacetate (LTA) oxidation of 4-tert-butyl-4-penten-1-ol (3) in boiling benzene afforded the tetrahydrofuran (THF) acetoxy ether 7 (78%) as the main product, while the acetoxylated tetrahydropyran (THP) ether (13) was obtained in a substantially lower yield (12.5%). The main products of the LTA oxidation of 4-tert-butyl-1-pentanol (4) also include the acetoxylated THF ether 7 (19.6%). The "normal" cyclization product, i.e., the THF ether 29, was obtained in 18.2% yield.