Tetrahedron

Ion pairing effects on the regioselectivity of arylic versus benzylic C–O bond reductive cleavage: synthetic applications

U Azzena, G Dettori, I Mascia, L Pisano, M Pittalis

文献索引：Azzena, Ugo; Dettori, Giovanna; Mascia, Ilaria; Pisano, Luisa; Pittalis, Mario Tetrahedron, 2007 , vol. 63, # 48 p. 11998 - 12006

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被引用次数: 15

摘要

The regioselectivity of the reductive cleavage of 3, 4, 5-trimethoxybenzyl methyl ether strongly depends on the alkali metal employed as a reducing agent and solvent effects. Reactions run using Na as a reducing agent led to aromatic C (4)–O bond cleavage, whilst reductions run in the presence of Na/15-crown-5, or using Li as a reducing agent, led to highly regioselective benzylic C–O bond cleavage. This regioselectivity turnaround is ...