Mn(III)acetate-mediated additions of active methylene compounds to bicyclic olefins: Synthesis of bicyclic olefin-fused dihydrofurans

摘要

Bicyclic alkenes such as benzonorbornadiene, oxabenzonorbornadiene, norbornene, and norbornadiene were reacted with 1,3-cyclohexanedione and ethyl acetoacetate in the presence of Mn(OAc)(3) and Cu(OAc)(2). Except for the reaction of benzonorbornadiene and ethyl acetoacetate, dihydrofuran derivatives were the only products obtained. The formation of naphthalene derivatives was observed together with dihydrofuran in the aforementioned benzonorbornadienefethyl acetoacetate reaction. Additionally, the dihydrofuran product from the addition of ethyl acetoacetate to norbornadiene was slowly converted into epoxide derivative with air. The mechanism for the formation of the products is discussed. (C) 2019 Elsevier Ltd. All rights reserved.