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Paper | Regular issue | Vol 38, No. 5, 1994, pp.991-1000
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6633
Chromenes and Chromanones. Part I The Birch Reduction of Coumarins and 2H-Chromenes

Miroslaw Aniol, Przemyslaw Lusiak, and Czeslaw Wawrzenczyk*

*Institute of Fundamental Chemistry, Agricultural University , Norwida 25, 50-357 Wroclaw, Poland


The reduction of coumarin, 4-methylcoumarin, 2,2-dimethyl-2H-chromene and 2,2,4-trimethyl-2H-chromene with sodium or lithium in liquid ammonia with the presence or without donor of protons was carried out. The formation of phenolic products was observed when a limited amount of alcohol as a proton donor was present in the reaction medium. In the experiments with excess of alcohol the products with a partially reduced benzene ring were formed.