Open AccessThe Opening of the Cyclohexane Ring of Pinanones Using Baeyer-Villiger Conditions
Author(s) -
Alan F. Thomas,
Florence Rey
Publication year - 1991
Publication title -
chimia international journal for chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.1991.164
Subject(s) - cyclohexane , solvent , ring (chemistry) , chemistry , reaction conditions , organic chemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , catalysis
Reaction of nopinone (1) with 3-chloroperbenzoic acid in CHCl3 leads, in a very slow reaction, to the two lactones 2 and 3 in the ratio 9:1. Methylnopinone (4) under the same conditions gives the homologous lactones 6 and 7, but in the reverse ratio, together with minor amounts of the stereoisomers 8 and 9 arising from the presence of a small amount of the trans-isomer in the starting material. For the successful isolation of some of these lactones, it is essential to remove all traces of EtOH from the solvent CHCl3.
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