1991
DOI: 10.1080/10412905.1991.9697924
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The Essential Oil ofCalamintha arkansana(Nutt.) Shinners

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Cited by 8 publications
(1 citation statement)
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“…Geranylbarium (77), which can be obtained209 by reacting geranyl chloride (78) with equirnolar Reike barium in tetrahydrofuran at -78 "C, can be coupled with the geraniolderived bromide (79) to yield geranylgeraniol (80) without disturbance of alkene geometry.210 After appropriate chemistry, the sequence can be repeated to synthesise higher homologues. Citronella1 (53) reacts rapidly with diethanolamine to give (81) which undergoes hydration and then hydrolysis in the presence of sulfuric acid to give the hydroxy-aldehyde (82) without significant competing cyclisation.211 Reaction of (R)citronellyl acetate (83) with thionyl chloride at -20 "C in the presence of catalytic Et2A1C1 and then with methanol yields the rearranged allylic sulfinate ester (84) via an ene-type process. Geranyl and linalyl acetates behave analogously.212 Linalool (25) reacts with thiourea in the presence of hydrohalic acids to give geranyl thiol (85) after basic hydrolysis of the thiouronium salt which is formed.213…”
Section: I ! Nmentioning
confidence: 99%
“…Geranylbarium (77), which can be obtained209 by reacting geranyl chloride (78) with equirnolar Reike barium in tetrahydrofuran at -78 "C, can be coupled with the geraniolderived bromide (79) to yield geranylgeraniol (80) without disturbance of alkene geometry.210 After appropriate chemistry, the sequence can be repeated to synthesise higher homologues. Citronella1 (53) reacts rapidly with diethanolamine to give (81) which undergoes hydration and then hydrolysis in the presence of sulfuric acid to give the hydroxy-aldehyde (82) without significant competing cyclisation.211 Reaction of (R)citronellyl acetate (83) with thionyl chloride at -20 "C in the presence of catalytic Et2A1C1 and then with methanol yields the rearranged allylic sulfinate ester (84) via an ene-type process. Geranyl and linalyl acetates behave analogously.212 Linalool (25) reacts with thiourea in the presence of hydrohalic acids to give geranyl thiol (85) after basic hydrolysis of the thiouronium salt which is formed.213…”
Section: I ! Nmentioning
confidence: 99%