Functionalization of oxabenzonorbornadiene: Manganese(III)-mediated oxidative addition of dimedone

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2017-09-01

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ÇALIŞKAN, Raşit
Sari, Ozlem
Balcı, Metin

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3-Chloro-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)-3-hydroxy-5,5-dimethylcy-clohex- 2-en-1-one, synthesized by the reaction of oxabenzonorbornadiene with Mn(OAc)(3) and dimedone in the presence of HCl in acetic acid, was submitted to ring-opening reactions with BBr3 and H2SO4. Reaction with BBr3 yielded 2 products, a 5-membered ring and an 8-membered ring, with the former being the major product. However, the H2SO4-supported reaction exclusively formed an 8-membered ring. The mechanism of formation of these products was supported by theoretical calculations.

Subject Keywords

Physical and Theoretical Chemistry, Organic Chemistry

URI

https://hdl.handle.net/11511/57022

Journal

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

DOI

https://doi.org/10.1002/poc.3720

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

R. ÇALIŞKAN, O. Sari, and M. Balcı, “Functionalization of oxabenzonorbornadiene: Manganese(III)-mediated oxidative addition of dimedone,” JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, pp. 0–0, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57022.