Radical cyclization reactions mediated by manganese(III) acetate were carried out with p-excessive alkenes (2a-d) and 3-oxopropanenitriles (1a-f) resulting in the formation of 3-cyano-4,5-dihydrofuran derivatives in poor to high yields. A mechanism was proposed for the cyclization reaction. The significance of the study is the formation of the 3-cyano-4,5-dihydrofuran derivatives resembling terfuran, 2-(2-thienyl)furan and 2-(2-benzofuryl)furyl compounds having the fluorescent properties due to a conjugated p-electron system particularly containing the cyano moeity.
Radical cyclization reactions of both aliphatic 1,3‐diones 1a and 1b and of cyclic 1,3‐diones 1c–1e with 2‐thienyl‐ and 3‐thienyl‐substituted alkenes 2a–2d in the presence of manganese(III) acetate were investigated. Thienyl‐substituted dihydrofurans 3 were obtained with moderate to high yields (Table 1–3). Also, the favorable effect of the thienyl substituent on the intermediate carbocation stability was evaluated by comparison with a phenyl substituent.
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