Uncommon Ozonolysis of 2,3-Seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile

Uncommon Ozonolysis of 2,3-Seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile

The oxidation of 2,3-seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile with ozone in methylene chloride at –40°C afforded a mixture of 4,20-dioxo-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicar­bonitrile (71%), 4,20-dioxo-3,30-dihydroxy-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicarbonitril...

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Veröffentlicht in:Russian journal of organic chemistry 2021-09, Vol.57 (9), p.1412-1416
Hauptverfasser: Khusnutdinova, E. F., Baikova, I. P., Lobov, A. N., Kazakova, O. B.
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry and Materials Science
Dichloromethane
NMR spectroscopy
Organic Chemistry
Oxidation
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Zusammenfassung:The oxidation of 2,3-seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile with ozone in methylene chloride at –40°C afforded a mixture of 4,20-dioxo-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicar­bonitrile (71%), 4,20-dioxo-3,30-dihydroxy-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicarbonitrile (15%), 2,17-dicyano-2,4-seco-3,23,24,28,29,30-hexanorlupane-4,20-dioic acid (7%), and 30-hydroxy-2,4-seco-3,23,24,28,29-pentanorlupan-4-oic acid (4%). The product structure was determined by NMR spectroscopy using two-dimensional shift correlation techniques.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428021090049