1971
DOI: 10.1139/v71-286
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On the Isolation of (+)3-Thujone

Abstract: Conditions necessary for the formation of the (+)3-thujone bisulfite adduct 1a and its utilization for the isolation of pure (+)-thujone have been established.

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Cited by 9 publications
(7 citation statements)
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“…Brominution of ( -)-4-Chlorothujone (9): ( -)-( 1 S,2S,4R,5S)-2-Bromo-4-chlorothujan-3-one (12) and ( -)-( 1 S,2R,4R,5S)-2-Bromo-4-chlorothujan-3-one (13).-Bromine (6.15 g, 0.95 mol equiv.) in carbon tetrachloride (1 5 ml) was added during 40 min to a stirred solution of (-)-4-chlorothujone (7.6 g) in carbon tetrachloride (30 ml).…”
Section: ) Work-up Gave a Productmentioning
confidence: 99%
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“…Brominution of ( -)-4-Chlorothujone (9): ( -)-( 1 S,2S,4R,5S)-2-Bromo-4-chlorothujan-3-one (12) and ( -)-( 1 S,2R,4R,5S)-2-Bromo-4-chlorothujan-3-one (13).-Bromine (6.15 g, 0.95 mol equiv.) in carbon tetrachloride (1 5 ml) was added during 40 min to a stirred solution of (-)-4-chlorothujone (7.6 g) in carbon tetrachloride (30 ml).…”
Section: ) Work-up Gave a Productmentioning
confidence: 99%
“…Early fractions gave ( -)-( 1S,2R,4R,5S)-2-bromo-4-chlorothujan-3-one (13) (2.8 g), which after a second run through a column was obtained as a liquid, [a]Dz2 -262" ( c 0.74); vmaX,(L) 3 520, 1 774, 775, and 655 cm-' ; 6,O. 38 ( 1 H, dd, J 7,4 Hz, ~x -H ) , Equilibration of ( -)-( 1 S,2S,4R,5S)-2-Bromo-4-chlorothujan-2one (12) with its 3-Epimer (13).-A mixture of the bromo chloro ketone (12) (0.4 g), finely powdered pyridinium bromide (1 g) and dimethyl sulphoxide (2 ml) was stirred at room temperature for 60 h. Work-up gave a pale brown oil (0.4 g), [%IDzo -195" (c 3.4); vmax,(L) 1 770 cm-'. Its 'H n.m.r.…”
Section: ) Work-up Gave a Productmentioning
confidence: 99%
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