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Medium Effects on C,C‐Bond Cleavage in the Alcohol Oxidation with Chromic Acid
Author(s) -
Müller Paul,
Blanc Jacky
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620627
Subject(s) - chemistry , chromic acid , acetone , oxalic acid , acetic acid , yield (engineering) , ketone , bond cleavage , alcohol , medicinal chemistry , cleavage (geology) , alcohol oxidation , organic chemistry , catalysis , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
The C,C‐bond cleavage which occurs during chromic acid oxidation of t ‐butylphenylmethanol (1) and 1,2‐diphenylethanol (2) to the extent of up to 67% is reduced to 3% for 1 and 13% for 2 when the reaction is run in acetone, and totally suppressed upon co‐oxidation of the alcohols 1 and 2 with oxalic acid. Similarly, the yield of 7‐norbornanone obtained from 7‐norbornanol (7) is raised in going from acetic acid (24%) to acetone (41%) and approaches 100% in the co‐oxidation. With the co‐oxidation 5‐ endo ‐bicyclo [2.1.1]hexanol (3) is converted to the corresponding ketone in 54% yield. Mechanistic implications of these results are discussed.
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