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Zur Kenntnis ätherischer Öle. 2. Mitteilung. Die Struktur der sogenannten «Linalooloxide»
Author(s) -
Felix Dorothee,
Melera A.,
Seibl J.,
Kováts E. Sz.
Publication year - 1963
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.19630460507
Subject(s) - diastereomer , chemistry , tetrahydrofuran , stereochemistry , medicinal chemistry , organic chemistry , solvent
Monoperphtalic acid oxidizes (−)‐linaloöl in the cold to the expected diastereomeric pair of 6,7‐dihydro‐6,7‐epoxy‐linaloöls. These substances are unstable. On heating or on treatment with acid they are converted to a mixture of two pairs of diastereomeric oxides C 10 H 18 O 2 . The pair A/B, amounting to about 90% of the secondary product, are known as the linaloöl‐oxides. They are shown to be tetrahydrofuran derivatives with the structures IV A and IV B. The pair C/D are diastereomeric tetrahydrophyran derivatives of the structures III C and III D.