Molecular Iodine as an Optimal Catalyst of Alkene Migration in Sesquiterpene Lactones to a Hindered endo-Position

Trifluoroacetic acid has induced the migration of the Δ 4,14 exo -double bond of isoalantolactone to the endo -position (Δ 4 ) with the formation of alloalantolactone. Different conditions theoretically leading to the conversion of isoalantolactone into its synthetically less accessible isomer with...

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Bibliographic Details
Published in:Russian journal of general chemistry 2022-08, Vol.92 (8), p.1392-1400
Main Authors: Semakov, A. V., Brel, V. K.
Format: Article
Language:English
Subjects:
Chemical properties
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Conversion
Formic acid
Iodine
Isomerization
Isomers
Lactones
Olefins
Perchloric acid
Refluxing
Sulfuric acid
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Summary:Trifluoroacetic acid has induced the migration of the Δ 4,14 exo -double bond of isoalantolactone to the endo -position (Δ 4 ) with the formation of alloalantolactone. Different conditions theoretically leading to the conversion of isoalantolactone into its synthetically less accessible isomer with a double bond in position Δ 3 (sulfuric acid, perchloric acid, formic acid, microwave irradiation of the lactone adsorbed on various carriers) have been screened. Refluxing of isoalantolactone with iodine has led to rapid conversion with predominant formation of lactone isomers with a double bond in positions Δ 3 and Δ 4 in approximately equal yield. Molecular iodine has also turned out to be the optimal agent for the isomerization of dehydrocostus lactone.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363222080059