Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Solvolysis of Δ1,9-10-hydroxymethyl-octaline benzenesulfonate (XIII) yields as the chief product [0,1,4,4]-Δ1-tricyclo-undecene (XV), the structure of which was subsequently proven by chemical means. In a competing reaction involving molecular rearrangement some bicyclic compound XVI is also found. Similarly Δ12-18, 28-cyclo compounds have been isolated in the solvolysis of Δ13,18-28-mesylates or benzenesulfonates of the oleanane series, thus supporting the view that homoallylic ring closure is the major reaction occurring in the solvolysis of compounds which contain the Δ1,9-10-hydroxymethyl-octaline system.
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