The Journal of Organic Chemistry

Substituent effects on hydrogenation of aromatic rings: hydrogenation vs. hydrogenolysis in cyclic analogs of benzyl ethers

L Anzalone, JA Hirsch

文献索引：Anzalone, Luigi; Hirsch, Jerry A. Journal of Organic Chemistry, 1985 , vol. 50, # 12 p. 2128 - 2133

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被引用次数: 55

摘要

Carbalkoxy substituents are shown to retard the hydrogenation of aromatic rings over Rh/C catalyst. Hydrogenolysis predominates with acyclic (benzy1oxy) acetates over this catalyst, but both hydrogenation and hydrogenolysis become sluggish with 2-isochroman-4-ones (1). However, phthalides may be cleanly hydrogenated in moderate to excellent yields without significant hydrogenolysis. Placing a benzyl ether in a ring system appears to greatly ...