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Solvolyseversuche bei Verbindungen vom Typus des Δ 1,9 ‐10‐Hydroxymethyl‐octalins
Author(s) -
Rowe J. W.,
Melera A.,
Arigoni D.,
Jeger O.,
Ruzicka L.
Publication year - 1957
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19570400102
Subject(s) - solvolysis , chemistry , hydroxymethyl , bicyclic molecule , medicinal chemistry , stereochemistry , ring (chemistry) , hydrolysis , organic chemistry
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.