Studies in regiospecific oxidation reactions of 1-methyl-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione.

Baeyer-Villiger oxidation of 1-methylpentacyclo[5.4.0.02,6.03,10.05,9] undecane-8,11-dione, performed by using m-chloroperbenzoic acid in 1:1 molar ratio, resulted in the formation of monolactone. The corresponding dilactone, was synthesized by reacting 1-methyl-PCU-8,11-dione with m-chloroperbenzoic acid in 1:2 molar ratio. 6-Methyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione was converted into the corresponding exo-6,7-monoepoxide via treatment with 30% aqueous hydrogen peroxide. Epoxidation of this monoepoxide by using m-chloroperbenzoic acid afforded the corresponding bis-epoxide. Ceric ammonium nitrate (CAN) promoted oxidation of 1-methyl-PCU-8,11-dione afforded "methylated lactones" and a "methylated alkene."

Grantor dc:publisher

University of North Texas

Year dc:date

2004

Author dc:creator

• Vappala, Indu

Contributors dc:contributor

• Marchand, Alan P.
• Thomas, Ruthanne D.

• Lactones.
• Oxidation.
• m-chloroperbenzoic acid
• epoxidation
• monolactone
• PCU
• CAN

Statement dc:rights

• Public
• Copyright
• Vappala, Indu
• Copyright is held by the author, unless otherwise noted. All rights reserved.

Language dc:language

English

Identifier

oclc: 55804170
https://digital.library.unt.edu/ark:/67531/metadc4478/
ark: ark:/67531/metadc4478

OAI identifier oai:identifier

info:ark/67531/metadc4478