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Reduction of Ketones by Alkali Metals in Tertiary Alcohols: Unexpected Cation Effect on the Stereochemistry
Author(s) -
Giordano Claudio,
Perdoncin Giulio,
Castaldi Graziano
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198504991
Subject(s) - chemistry , ketyl , alkali metal , rubidium , protonation , potassium , medicinal chemistry , caesium , tertiary alcohols , inorganic chemistry , organic chemistry , alcohol , ion , radical
An increase in the ratio of 1 to 2 from 80:20 to 95:5 can be obtained when the reactant, a 7‐ketosteroid, is reduced with K, Rb, or Cs instead of with Na in tertiary alcohols. A similar result is observed on reduction with Na in the presence of potassium, rubidium, or cesium salts. The effect could be ascribed to a C ‐protonation of the ketyl initially formed in the reaction.