Intermolecular proton transfer from bicyclooctyl carbonium ion to cyclooctadiene

✍ Scribed by I. Tabushi; K. Fujita; R. Oda

• Book ID: 104241052
• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 204 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89787-2

✦ Synopsis

In our current study on R-X cyclleatlon of 018, cls-1,5-cyclooctadlene by catlonic addition(l), It Is concluded that remarkable Intermolecular proton transfer from &substituted blcyclo[3,3,0] act-2-.9oarbonlum ion to the diene should be Involved. Addition of dlacetoxymethane to cyclooctadlene (equlmolar amount) in the presence of Lewis acid such as ZnClz or BP3 (UP to 20 moL to the reactants) gave a considerable amount of monoacetate mixture (13.l;;tyleld of bp 72O/'@u~Hg) together with normal addition-cycllzatlon products( The monoacetate mixture was consisted of exo-(I) and endo-cls-blcyclo[3,3,O]octyl -2-acetate (II) (4% and 34;6, respectively) and exo-blcyclo[3,2,1]octyl-8 -acetate (III) (1%). Structural assignment of these was made on comarlson of VPC and IR, and nmr spectra of these with those of authentic I(2), II(2) and