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

Jih Ru Hwu, Vincent Chua, Jean E. Schroeder, Richard E. Barrans Jr., Kevin P. Khoudary, Naelong Wang and John M. Wetzel
Journal of Organic Chemistry, Vol.51(24), pp.4731-4733
1986

Abstract

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 + → Ca 2+ + e - processes are 4.6 and 47 times greater, respectively, than that afforded by the Li → Li + + e - process. © 1986 American Chemical Society.

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