Lead tetraacetate oxidation of bridged bicyclic alcohols

✍ Scribed by Keizo Kitahonoki; Akio Matsuura

• Publisher: Elsevier Science
• Year: 1964
• Tongue: French
• Weight: 165 KB
• Volume: 5
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71699-6

✦ Synopsis

IN recent years, the oxidation of monohydric alcohols to tetrohydrofuran derivatives by lead tetraacetate has been studied extensively in steroids and used successfully to functionalize the "unactivated" Cl* or Ctp angular methyl group (1,2). We have applied this type of reaction in the bridged ring compounds. Quite recently, Mariarty and Kapadia (3) reported on the oxidation of bicyclo[ 2.2.1 1 hept-5-ene-2-methanol (I) to the ether-acetate (II) by lead tetraacetate. The report prompts us to describe our results on the dxidation of saturated bridged alcohols by the same reagent. When a solution of bicyclo[ 2.2.2]octane-2-methanol (Ill) and lead tetraacetate in benzene was heated under reflux for 12 hours until the starting material could no longer be detected, perhydro-3,6-methanobenzofuran (IV), m.p. 147-148' , was obtained in 42.9% yield*3 along with the acetate of the starting alcohol *1 *2 *3 Bridaed Rina Compounds, Part II; Part I of this series: K. Kitahonoki and Y.