Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene
Tetrahedron, cilt.73, sa.4, ss.291-297, 2017 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 73 Sayı: 4
- Basım Tarihi: 2017
- Doi Numarası: 10.1016/j.tet.2016.11.061
- Dergi Adı: Tetrahedron
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.291-297
- Anahtar Kelimeler: Benzonorbornadiene, Copper(II) acetate, Cycloaddition, Dihydrofurans, Manganase(III) acetate, Oxabenzonorbornadiene, Oxidation, Rearrangement
- Isparta Uygulamalı Bilimler Üniversitesi Adresli: Hayır
Özet
Benzonorbornadiene and 7-oxabenzonorbornadiene were reacted with Meldrum's acid and dimethyl malonate in the presence of Mn(OAc)3and Cu(OAc)2in 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.