76609-13-7Relevant academic research and scientific papers
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.
Formation of 1,2-Dioxanes by the Use of Tris(2,4-pentanedionato)manganese(III) or Manganese(III) Acetate
Nishino, Hiroshi,Tategami, Shin-ichi,Yamada, Takashi,Korp, James D.,Kurosawa, Kazu
, p. 1800 - 1809 (2007/10/02)
The reactions of 1,1-diphenylethene, 1,1-bis(4-chlorophenyl)ethene, 1,1-bis(4-methoxyphenyl)ethene, 1,1-bis(4-methylphenyl)ethene, 1,1-bis(4-fluorophenyl)ethene, styrene, 1-octene, cyclohexene, and cyclooctene with tris(2,4-pentanedionato)manganese(III) () in acetic acid at room temperature give 4-acetyl-3-methyl-1,2-dioxan-3-ol in 8-92percent yields, together with 3-acetyl-4-hydroxy-3-hexene-2,5-dione.The similar reactions of 1,1-diphenylethene with 2,4-pentanedione, 3-methyl-2,4-pentanedione, 3-ethyl-2,4-pentanedione, 1-phenyl-1,3-butanedione, acetoacetanilide, and 1,3-cyclohexanedione in the presence of manganese(III) acetate also give the corresponding cyclic peroxide in good to moderate yields.The mechanisms of manganese(III)-induced 1,2-dioxane ring formation and concomitant radical side reaction are discussed.
Epoxides : Part II - Synthesis of Butyrolactones
Moussa, G. E. M.,Basyouni, M. N.,Shaban, M. E.
, p. 800 - 801 (2007/10/02)
1,1-Diarylethylene oxides (Ia-c) react with diethyl malonate in the presence of sodium ethoxide to give γ,γ-diaryl-α-ethoxycarbonyl-γ-butyrolactones (IIa-c) which yield the carboxylactones (IIIa-c) upon alkaline hydrolysis.Decarboxylation of IIIa-c furnishes the corresponding γ,γ-diaryl-γ-butyrolactones (IVa-c).
