Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions.
Topologically mobile difluorinated cyclooctenones undergo rapid, high-yielding, and completely stereoselective epoxidations with methyl(trifluoromethyl)dioxirane. The epoxides resist conventional hydrolysis but react smoothly in basic media under microwave irradiation to afford unique hemiacetals and hemiaminals in good yield. [reaction: see text]
Fawcett
John
J
Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, United Kingdom.
Griffith
Gerry A
GA
Percy
Jonathan M
JM
Uneyama
Emi
E
D000080:Acetals / Q000737:chemistry; D002625:Chemistry, Organic; D003512:Cyclohexanones / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005027:Ethylene Oxide / Q000031:analogs & derivatives* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D006868:Hydrolysis; D008872:Microwaves; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000080:Acetals; D003512:Cyclohexanones; D004852:Epoxy Compounds; D005461:Fluorine; C445840:methyl(trifluoromethyl)dioxirane; D005027:Ethylene Oxide