24234-76-2Relevant academic research and scientific papers
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
A new method for the regio and stereoselective hydrocarboxylation of alkynes using NaHFe(CO)4/CH2Cl2 system
Periasamy, Mariappan,Radhakrishnan, Ukkiramapandian,Rameshkumar, Chellappan,Brunet, Jean-Jacques
, p. 1623 - 1626 (1997)
The reagent generated in situ in THF using NaHFe(CO)4 and CH2Cl2 was used for the regio and stereoselective hydrocarboxylation of terminal and internal alkynes to obtain α,β-unsaturated carboxylic acid derivatives.
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.
Double carbonylation of alkynes using NaHFe(CO)4
Periasamy, Mariappan,Radhakrishnan, Ukkiramapandian,Brunet, Jean-Jacques,Chauvin, Remi,El Zaizi, Abdel Wahed
, p. 1499 - 1500 (1996)
The reagent generated in situ using NaHFe(CO)4 and MeI in THF, on reaction with alkynes followed by CuCl2 oxidation, gives the corresponding cyclobutenediones in moderate yields (27-42%) in addition to the corresponding α,β-unsaturated carboxylic acids (10-22%).
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.
Reactive iron carbonyl reagents via reaction of metal alkoxides with Fe(CO)5 or Fe2(CO)9: Synthesis of cyclobutenediones via double carbonylation of alkynes
Beesu, Mallesh,Periasamy, Mariappan
experimental part, p. 543 - 549 (2011/04/16)
Alkoxy bases such as t-BuOK react with Fe(CO)5 to give reactive iron carbonyl intermediates that in turn react with alkynes at 70 °C in THF to give 1,2-cyclobutenediones in 70-93% yields after CuCl2· 2H2O oxidation. A novel 1,2-diacyloxyferrole derivative was isolated in the reaction of diphenylacetylene with Fe(CO)5/t-BuOK in the presence of acetyl chloride in contrast to the formation of a 1,4-diacyloxyferrole complex formed in the reaction using Fe(CO) 5/Me3NO. The Fe2(CO)9/t-BuOK reagent system also converts the alkynes to corresponding cyclobutenediones in 63-90% yields under similar reaction conditions.
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.
Pd-catalyzed, Cu(I)-mediated cross-couplings of bisarylthiocyclobutenediones with boronic acids and organostannanes
Aguilar-Aguilar, Angelica,Liebeskind, Lanny S.,Pena-Cabrera, Eduardo
, p. 8539 - 8542 (2008/03/11)
(Chemical Equation Presented) Bisarylthiocyclobutenedione 7 reacted smoothly with a variety of both organostannanes and (hetero)arylboronic acids in the presence of a catalytic amount of Pd and a stoichiometric amount of CuTC to produce symmetrical disubstituted cyclobutenediones in yields that range from 37 to 94% (18 examples).
Amine induced carbonylation of alkynes to cyclobutenediones using Fe3(CO)12
Rameshkumar, Chellappan,Periasamy, Mariappan
, p. 2719 - 2722 (2007/10/03)
Iron carbonyl species, prepared in situ in THF using Fe3(CO)12, react with alkynes at 25°C, in the presence of certain amines, to give the corresponding cyclobutenediones in moderate to good yields (25-61%) after CuCl2·2H
Ladderane-like motifs: Solid state architecture of trans-1,2-diphenyl-1- cyclobutene-3,4-diol dinitrate
Mehta, Goverdhan,Uma
, p. 1154 - 1158 (2007/10/03)
C2-Symmetric trans-1,2-diphenyl-1-cyclobutene-3,4-diol dinitrate defines a novel ladderane-like motif in the solid state through a network of C-H...O interactions between aromatic C-H donor and a weak acceptor like the nitrate ester group.
