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An Anomalous Oxidation of β‐Pinene
Author(s) -
Jefford Charles W.,
Roussel Albert,
Evans Samuel M.
Publication year - 1975
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.19750580727
Subject(s) - chemistry , potassium permanganate , pinene , periodate , catalysis , permanganate , aqueous solution , organic chemistry , bicyclic molecule , product (mathematics) , medicinal chemistry , mathematics , geometry
The oxidation of β‐pinene with aqueous alkaline potassium periodate and catalytic amounts of potassium permanganate gave, in addition to the expected oxidation product nopinone, a β‐ketol. The structure of the latter was shown to be 1‐(2‐hydroxyisopropyl)bicyclo[3.1.0]hexan‐2‐one. The formation of this anomalous side‐product represents a new type of rearrangement of the pinane skeleton.