Calcium in liquid ammonia for the reduction of benzyl ethers. Mechanistic clues derived from chemoselectivity studies

…, V Chua, JE Schroeder, RE Barrans Jr…

Index: Hwu, Jih Ru; Chua, Vincent; Schroeder, Jean E.; Barrans, Richard E.; Khoudary, Kevin P.; et al. Journal of Organic Chemistry, 1986 , vol. 51, # 24 p. 4731 - 4733

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Citation Number: 37

Abstract

Summary: Extremely high selectivity was provided by calcium in liquid ammonia in the cleavage of the benzylic carbon-oxygen bond in benzyl ethers containing various other functionalities. Results of controlled experiments indicate that the selectivities offered by the Ca-Ca++ e-and the Ca+-Ca2++ e-processes are 4.6 and 47 times greater, respectively, than that afforded by the Li-Li++ e-process.