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Solvolyseversuche bei Verbindungen vom Typus des Δ1,9-10-Hydroxymethyl-octalins

✍ Scribed by J. W. Rowe; A. Melera; D. Arigoni; O. Jeger; L. Ruzicka


Book ID
102856725
Publisher
John Wiley and Sons
Year
1957
Tongue
German
Weight
825 KB
Volume
40
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

Solvolysis of Δ^1,9^‐10‐hydroxymethyl‐octaline benzenesulfonate (XIII) yields as the chief product [0,1,4,4]‐Δ^1^‐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 Δ^12^‐18, 28‐cyclo compounds have been isolated in the solvolysis of Δ^13,18^‐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 Δ^1,9^‐10‐hydroxymethyl‐octaline system.