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

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ÇALIŞKAN R., Sari O., BALCI M.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, vol.30, no.9, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 30 Issue: 9
  • Publication Date: 2017
  • Doi Number: 10.1002/poc.3720
  • Journal Name: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Middle East Technical University Affiliated: Yes

Abstract

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.