28799-40-8Relevant academic research and scientific papers
Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D
Ha, Tu M.,Chatalova-Sazepin, Claire,Wang, Qian,Zhu, Jieping
supporting information, p. 9249 - 9252 (2016/08/05)
A copper-catalyzed three-component reaction of alkenes, alkylnitriles, and water affords γ-butyrolactones in good yields. The domino process involves an unprecedented hydroxy-cyanoalkylation of alkenes and subsequent lactonization with the creation of three chemical bonds and a quaternary carbon center. The synthetic potential of this novel [2+2+1] heteroannulation reaction was illustrated by a concise total synthesis of (±)-sacidumlignan D.
The Reaction of Arylmagnesium Halides with Succinic Anhydride
Rahman, M. T.,Nur, H. P.
, p. 469 - 474 (2007/10/02)
The reaction of equimolar amounts of phenylmagnesium bromide and succinic anhydride in THF at -78 deg for 2 h gives subsequent to hydrolytic work-up, 3-benzoylpropionic acid in 76percent yield and 4,4-diphenyl-4-butyrolactone in 3percent yield.When two molar equivalents of the Grignard reagent are employed, the yields of these products are respectively 85 and 14percent.On the other hand, when four equivalents of the Grignard reagent are employed for every equivalent of succinic anhydride at 66 deg C, a diketone, 1,4-diphenylbutane-1,4-dione is obtained in 72percent yield.Other products include 4,4-diphenyl-4-butyrolactone (19percent) and 3-benzoylpropionic acid (6percent).Under comparable conditions, 4-methyl- and 4-methoxyphenylmagnesium halides react similarly with succinic anhydride, giving fair yields (49-53percent) of the corresponding diketones.However, 4-chlorophenylmagnesium chloride only gives the keto-acid (12percent) and lactone (42percent), but no diketone.
