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Studies on the Radical Cyclization of 3‐Oxopropanenitriles and Alkenes with Cerium(IV) Ammonium Nitrate in Ether Solvents
Author(s) -
Yılmaz Mehmet
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000440
Subject(s) - chemistry , cerium , ether , ammonium nitrate , dimethoxyethane , manganese , solvent , medicinal chemistry , organic chemistry , electrolyte , electrode
The radical cyclization of 3‐oxopropanenitriles 1a – 1e and alkenes 2a – 2g with cerium(IV) ammonium nitrate (CAN) in ether solvents was investigated ( Tables 1 and 2 ). In the optimization study, 1,3‐dioxolane, 1,4‐dioxane, 1,2‐dimethoxyethane, Et 2 O, and THF were used as ether‐based solvents, and the latter was found to be the most effective solvent in radical cyclizations mediated by cerium(IV). This system (cerium(IV)/THF) was applied to cyclizations of various 3‐oxopropanenitriles and 1,3‐dicarbonyl compounds with alkenes resulting in the formation of 4,5‐dihydrofurans in high yields ( Table 2 and Scheme 2 ). The results of the cerium(IV)/THF radical cyclization were compared with those obtained with manganese(III) acetate/AcOH; the cerium(IV)/THF system turned out to be much more efficient.