24234-76-2Relevant articles and documents
Synthesis and characterization of cyclobutenedione-bithiophene π-conjugated polymers: Acetal-protecting strategy for Kumada-Tamao-Corriu coupling polymerization between aryl bromide and Grignard reagents
Ohishi, Tomoyuki,Sone, Takuma,Oda, Kohei,Yokoyama, Akihiro
, p. 40863 - 40872 (2019)
Cyclobutenedione is an aromatic ring that exhibits strong electron-withdrawing properties but is susceptible to undesired reactions with nucleophiles. Herein, Kumada-Tamao-Corriu coupling polymerization of a cyclobutenedione monomer whose carbonyl groups
New Convenient One-Pot Methods of Conversion of Alkynes to Cyclobutenediones or α,β-Unsaturated Carboxylic Acids Using Novel Reactive Iron Carbonyl Reagents
Periasamy, Mariappan,Rameshkumar, Chellappan,Radhakrishnan, Ukkiramapandian,Brunet, Jean-Jacques
, p. 4930 - 4935 (1998)
Reactions of NaHFe(CO)4/RX or [HFe3(CO)11]- reagents with alkynes lead to the formation of the corresponding α,β-unsaturated carboxylic acids and/or the cyclobutenediones. The reagent generated in situ using the NaHFe(CO)4/CH3I combination in THF, on reaction with alkynes followed by CuCl2·2H2O oxidation, gives the corresponding cyclobutenediones (27-42%) and α,β-unsaturated carboxylic acids (10-22%), whereas the reagent generated using CH2Cl2 in place of CH3I leads to α,β-unsaturated carboxylic acids (37-60%) and their derivatives (35-55%) at 25°C. The same reagent system in the presence of acetic acid (4 equiv) yields the corresponding cyclobutenedione (33%). The reaction using Me3SiCl gives the corresponding α,β-unsaturated carboxylic acids (45-54%) at 25°C and the corresponding cyclobutenediones (51-63%) at 60°C. Interestingly, the reaction of the [HFe3(CO)11]- species generated using Fe(CO)5/NaBH4/CH3COOH, with alkynes at 25°C, followed by CuCl2·2H2O oxidation gives the corresponding cyclobutenediones (60-73%). The possible intermediates and pathways for the formation of α,β-unsaturated carboxylic acids and cyclobutenediones are discussed.
Silver catalyzed decarbonylative [3 + 2] cycloaddition of cyclobutenediones and formamides
Ali, Sajjad,Gao, Jinming,Liu, Zhigang,Wang, Pengcheng,Wang, Zhengshen,Yu, Ruirui,Zheng, Huaiji
, (2021/06/02)
As an important moiety in natural products, N,O-acetal has attracted wide attention in the past few years. An efficient method to construct N,O-acetal has been developed. Using silver catalyst, cyclobutenediones were smoothly converted to the corresponding γ-aminobutenolides in the presence of formamides, in which cyclobutenediones likely proceed with a key decarbonylative [3 + 2] cycloaddition process. In this way, a series of products with varied substituents were isolated in moderate yield and fully characterized.
A simple and convenient method for the synthesis of cyclobutenediones from alkynes using new Fe(CO)5/NaH/MeI reagent system
Periasamy, Mariappan,Beesu, Mallesh,Shyam Raj
, p. 2843 - 2846 (2008/12/21)
Iron carbonyl complexes prepared in situ using the Fe(CO)5/NaH/MeI reagent combination and alkynes at 25 °C give the corresponding cyclobutenediones in 50-65% yields after CuCl2 · 2H2O oxidation.
