Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene

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• 作者：Raşit Ç ; alışkan^a ; ^{rasitcaliskan@sdu.edu.tr} ; Neslihan Nohut^a ; Ö ; zlem Yılmaz^a ; Ertan Sahin^b ; Metin Balci^c ;
• 关键词：Manganase(III) acetate ; Copper(II) acetate ; Cycloaddition ; Oxidation ; Dihydrofurans ; Rearrangement ; Benzonorbornadiene ; Oxabenzonorbornadiene
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：26 January 2017
• 年：2017
• 卷：73
• 期：4
• 页码：291-297
• 全文大小：737 K
• 卷排序：73

文摘

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.