Tetrahedron

Polar substituent effects in the sodium borohydride reduction of 2-and 3-substituted fluorenones

GG Smith, RP Bayer

Index: Smith,G.G.; Bayer,R.P. Tetrahedron, 1962 , vol. 18, p. 323 - 331

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Citation Number: 23

Abstract

The kinetics in the sodium borohydride reduction of fluorenone and twelve 2-and 3- substituted fluorenones were determined at three temperatures in isopropyl alcohol and the entropies and enthalpies of activation calculated. A linear Hammett σ ϱ plot was obtained using meta and para σ constants. The positive ϱ value (ϱ=+ 2· 65) confirmed the nucleophilicity of sodium borohydride. Deviations of the 2-methoxy and 2- ...