82084-27-3Relevant academic research and scientific papers
A Synthesis of 4-Oxo Carboxylic Acids, 4-Oxo Aldehydes, and 1,4-Diketones from γ-Lactones
Betancourt de Perez, Rosa M.,Fuentes, Lelia M.,Larson, Gerald L.,Barnes, Charles L.,Heeg, Mary Jane
, p. 2039 - 2043 (2007/10/02)
The α-methyldiphenylsilyl derivatives of γ-butyrolactone, γ-valerolactone, and the cis lactone of 2-hydroxycyclohexaneacetic acid have been reacted with Grignard reagents.The α-silylated lactones of γ-butyrolactone and γ-valerolactone react with a single equivalent of Grignard reagent to give a 2-substituted 4,5-dihydrofuran, which can be hydrolyzed and oxidized to 4-oxo carboxylic acids, 1,4-diketones, or 4-oxo aldehydes.The α-silylated fused lactone failed to react with ethylmagnesium bromide in refluxing tetrahydrofuran.An X-ray crystal structure of this silylated lactone indicated that this lack of reactivity is due to steric factors.
A FACILE SYNTHESIS OF 4-OXO CARBOXYLIC ACIDS FROM γ-BUTYROLACTONE
Fuentes, Lelia M.,Larson, Gerald L.
, p. 271 - 274 (2007/10/02)
An efficient, high-yield, three-step preparation of 4-oxo carboxylic acids from γ-butyrolactone via silylation and reaction with a Grignard reagent is presented.
