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Alkalische Spaltung und Benzilsäureumlagerung von 1,2,3‐Triketonen. 29. Mitt. über Reduktone und Tricarbonylverbindungen [1]
Author(s) -
Dao Huu Lé,
Dayer Francis,
Duc Laurent,
RodéGowal Heike,
Dahn Hans
Publication year - 1974
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.19740570738
Subject(s) - chemistry , steric effects , medicinal chemistry , cleavage (geology) , stereochemistry , geotechnical engineering , fracture (geology) , engineering
Under the conditions of the benzilic acid rearrangement diaryl und dialkyl 1,2,3‐triketones RCOCOCOR′ show two reactions: (1) Migration of RCO towards the more electronegative or less hindered CO group, yielding an α‐hydroxy‐β‐ketoacid which can undergo secondary reactions, and (2) direct cleavage between adjacent carbonyl groups forming RCOOH and R′CHOHCOOH, RCO being more electronegative or less hindered than R′CO. The balance between these reactions depends upon the steric and electronic properties of R and R′.