Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene. Issue 4 (26th January 2017)

• Record Type: Journal Article
• Authors: Çalışkan, Raşit; Nohut, Neslihan; Yılmaz, Özlem; Sahin, Ertan; Balci, Metin
• Is Part Of: Tetrahedron. Volume 73:Issue 4(2017)
• Page Start: 291
• Page End: 297
• Publication Date: 2017-01-26
• Subjects: Manganase(III) acetate -- Copper(II) acetate -- Cycloaddition -- Oxidation -- Dihydrofurans -- Rearrangement -- Benzonorbornadiene -- Oxabenzonorbornadiene; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.11.061
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Benzonorbornadiene and 7-oxabenzonorbornadiene were reacted with Meldrum's acid and dimethyl malonate in the presence of Mn(OAc)3 and Cu(OAc)2 in acetic acid. The reaction of benzonorbornadiene with Meldrum's acid gave a naphthalene derivative whereas the reaction with dimethyl malonate formed rearranged products derived from a carbocation intermediate. However, the reaction of 7-oxabenzonorbornadiene with Meldrum's acid gave two nonrearranged products. On the other hand, the reaction with dimethyl malonate unexpectedly formed a dihydronapthalene derivative with an unusual structure. The mechanism for the formation of the products is discussed. Graphical abstract: