150884-36-9Relevant academic research and scientific papers
Synthesis of sterically congested acetic acid derivatives: The reaction of hindered α-oxo esters with pentasubstituted aryl Grignard reagents
Hegarty,O'Neill
, p. 606 - 610 (2007/10/02)
The reactions of pentamethylphenylmagnesium bromide and pentachlorophenylmagnesium chloride with tert-butyl 2-oxo-3,3-dimethylbutanoate to give the 2-aryl-2-hydroxy-3,3-dimethylbutanoate esters were investigated. Attempted acid catalysed dealkylation of the tert-butyl 2-hydroxy-3,3-dimethyl-2-(pentamethylphenyl)butanoate to the corresponding acid was accompanied by skeletal rearrangement, while the corresponding pentachlorophenyl ester reacted normally. The corresponding α-pentachlorophenyl α-tertbutyl acetic acid 15 was synthesised without rearrangement. The reaction of pentachlorophenylmagnesium chloride with diisopropyl oxalate gave the α-oxo ester 18, which reacted with pentamethylphenylmagnesium bromide to afford the unsymmetrical diarylacetate ester 22. The corresponding acid chloride 25 could not be converted to the interesting unsymmetrical diarylketene 26.
