Baeyer-Villiger Oxidation of 1,7- & 1,9-dibromopentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

Baeyer-Villiger oxidation of 1,9-dibromopentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1,9-dibromo-PCU-8,11-dione) was performed by using an excess amount of m-chloroperbenzoic acid (3 equivalents) and resulted in the formation of the corresponding monolactone. The reaction would not proceed to the dilactone stage. The structure of the reaction product was established unequivocally via single crystal X-ray diffraction. Baeyer-Villiger oxidation of 1,9-dibromo-PCU-8,11-dione using ceric ammonium nitrate (CAN) was also performed and afforded a mixture of lactones. Only one of these lactones, which also contained an alkene functionality, could be isolated and characterized. 1,7-dibromo-PCU-8,11-dione was also reacted with CAN, yielding the mono-lactone, which has also been characterized.

Grantor dc:publisher

University of North Texas

Year dc:date

2004

Author dc:creator

• Akinola, Adeniyi O.

Contributors dc:contributor

• Thomas, Ruthanne D.
• Richmond, Michael

• Lactones.
• Oxidation.
• monolactone
• Baeyer-Villiger oxidations
• PCU-8
• 11-diones

Statement dc:rights

• Use restricted to UNT Community
• Copyright
• Akinola, Adeniyi O.
• Copyright is held by the author, unless otherwise noted. All rights reserved.

Language dc:language

English

Identifier

oclc: 55804158
https://digital.library.unt.edu/ark:/67531/metadc4471/
ark: ark:/67531/metadc4471

OAI identifier oai:identifier

info:ark/67531/metadc4471