528-34-7Relevant academic research and scientific papers
Scalable preparation and property investigation of a cis-cyclobutane-1,2-dicarboxylic acid from β-trans-cinnamic acid
Amjaour, Houssein,Wang, Zhihan,Mabin, Micah,Puttkammer, Jenna,Busch, Sullivan,Chu, Qianli R.
, p. 214 - 217 (2019)
Scalable synthesis of β-truxinic acid (CBDA-4) was accomplished by capturing and photodimerizing a metastable crystalline solid of trans-cinnamic acid. This synthetic approach builds a foundation for investigating the properties and applications of the us
Template-Directed Photochemical Homodimerization and Heterodimerization Reactions of Cinnamic Acids
Türkmen, Yunus Emre,Yagci, Bilge Banu,Zorlu, Yunus
, p. 13118 - 13128 (2021/09/18)
We developed a general method for the selective photochemical homo- and heterodimerization of cinnamic acid derivatives with the use of commercially available 1,8-dihydroxynaphthalene as a covalent template. A variety of symmetrical and unsymmetrical β-tr
Photocatalytic Oxidative [2+2] Cycloelimination Reactions with Flavinium Salts: Mechanistic Study and Influence of the Catalyst Structure
Hartman, Tomá?,Reisnerová, Martina,Chudoba, Josef,Svobodová, Eva,Archipowa, Nataliya,Kutta, Roger Jan,Cibulka, Radek
, p. 373 - 386 (2021/02/01)
Flavinium salts are frequently used in organocatalysis but their application in photoredox catalysis has not been systematically investigated to date. We synthesized a series of 5-ethyl-1,3-dimethylalloxazinium salts with different substituents in the positions 7 and 8 and investigated their application in light-dependent oxidative cycloelimination of cyclobutanes. Detailed mechanistic investigations with a coumarin dimer as a model substrate reveal that the reaction preferentially occurs via the triplet-born radical pair after electron transfer from the substrate to the triplet state of an alloxazinium salt. The very photostable 7,8-dimethoxy derivative is a superior catalyst with a sufficiently high oxidation power (E=2.26 V) allowing the conversion of various cyclobutanes (with Eox up to 2.05 V) in high yields. Even compounds such as all-trans dimethyl 3,4-bis(4-methoxyphenyl)cyclobutane-1,2-dicarboxylate can be converted, whose opening requires a high activation energy due to a missing pre-activation caused by bulky adjacent substituents in cis-position.
Donor-acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization
Chen, Feng,Chen, Hao,Liu, Xue-Fen,Luo, Shu-Ping,Ren, Chen-Chao,Wu, Qing-An,Xu, Liang-Xuan,Yu, Xiao-Cong
supporting information, p. 3707 - 3716 (2020/06/03)
Mild [2 + 2] photodimerization of enone substrates was induced by donor-acceptor fluorophores. Enone substrates were activated efficiently for anti-head to head dimerizations with a high yield (up to 83%) and high selectivity. The adjustable excited state potential also allows donor-acceptor fluorophores to be used for isomerization of the above substrates, confirming the potential of donor-acceptor fluorophores as energy transfer photocatalysts.
Using non-covalent interactions to direct regioselective 2+2 photocycloaddition within a macrocyclic cavitand
Nguyen, Nga,Clements, Aspen Rae,Pattabiraman, Mahesh
, p. 2433 - 2443 (2016/03/19)
The relative orientation of guests within ternary inclusion complexes is governed by the host-guest and guest-guest supramolecular interactions. Selectivity in 2+2 photocycloaddition between two alkenes included within a macrocyclic cavitand (γ-cyclodextrin) can be controlled using non-covalent interactions. In this manuscript, we report cavitand-mediated control of regioselectivity between alkyl cinnamates using non-covalent interactions. Using this method, we have shown that regioselectivity can be switched completely from a head-to-head dimer to a head-to-tail dimer. The reactions were also stereoselective in most cases. Stoichiometry experiments were performed to explore relative stabilities of the complexes, which indicate that the ternary complex is more stable than others. Selectivity in the photocycloaddition reaction was also applied retrospectively to deduce intermolecular orientations. Time-dependent conversion study we performed indicates that the observed reactivity of alkenes is representative of the intermolecular orientations in the bulk of the complex medium. Experimental observations and computational studies were used to qualitatively understand the complex structures, and relative magnitudes of the weak interactions. The reactions of complexes were studied in slurry form, and the extent of reaction control suggests a solid-state-like behavior.
γ-Cyclodextrin mediated photo-heterodimerization between cinnamic acids and coumarins
Clements, Aspen Rae,Pattabiraman, Mahesh
, p. 1 - 7 (2015/02/19)
The ability of γ-cyclodextrin to form ternary inclusion complexes has been utilized to mediate photo-heterodimerization between cinnamic acids and coumarins in the solid-state. Stabilizing steric and electronic interactions between the alkenes in the incl
Stereocontrolled photodimerization with congested 1,8-Bis(4′-anilino) naphthalene templates
Ghosn, Marwan W.,Wolf, Christia'
experimental part, p. 6653 - 6659 (2010/11/05)
Suzuki cross-coupling of a 1,8-dihalonaphthalene with 4-methoxy-3- methylphenylboronic acid or 4-acetamidophenylboronic acid and subsequent functional group transformation gave 1,8-bis(3′-methyl-4′-anilino) naphthalene, 16, and 1,8-bis(4′-anilino)naphthalene, 21, in 65% and 90% overall yield, respectively. These congested compounds exhibit two cofacial aniline rings that favor a proximate, parallel arrangement of covalently attached cinnamoyl units suitable for stereoselective photodimerization. The [2 + 2]cycloaddition was found to proceed with high yield and exclusive formation of cis,trans,cis-cyclobutane-1,2-dicarboxylic acids. Amide formation with cinnamoyl chloride and template 21 followed by photochemical dimerization and acidic hydrolysis gave β-truxinic acid, 10, in 69% overall yield. Coupling of 21 and (E)-3-(3,4-dimethylphenyl)acrylic acid in the presence of EDC, UV irradiation, and cleavage gave cis,trans,cis-3,4-bis(3,4-dimethylphenyl) cyclobutane-1,2-dicarboxylic acid, 26, in 60% yield. In both cases, the template was quantitatively recovered.
Temperature stability and photodimerization kinetics of β-cinnamic acid and comparison to its α-polymorph as studied by solid-state NMR spectroscopy techniques and DFT calculations
Fonseca,Hayes,Bluemich,Bertmer
, p. 5898 - 5907 (2008/12/23)
Photoreactions of the α- and β-polymorphs of trans-cinnamic acid were studied by 13C CPMAS solid-state nuclear magnetic resonance spectroscopy, and the reactants and products were spectroscopically characterized in detail. Chemical shifts and c
The interaction of Cinnamic acids with 60Co gamma radiation
Njus, Jeffrey M.,Sae-Lim, Chantana,Sandman, Daniel J.
, p. 55 - 61 (2008/02/04)
In the interest of expanding our knowledge of the interaction of cinnamic acid and its derivatives with ionizing radiation, (E)-cinnamic acid and several of its chlorinated and brominated derivatives were exposed to 60Co gamma radiation. Dimer yields were estimated from integration of the proton NMR signals of the irradiated material. (E)-Cinnamic acid itself is relatively unreactive. The largest yield of dimer was obtained with p-bromocinnamic acid where exposure to a dose of 116 megarads led to a 24% yield.
Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and γ-cyclodextrin
Pattabiraman, Mahesh,Natarajan, Arunkumar,Kaanumalle, Lakshmi S.,Ramamurthy
, p. 529 - 532 (2007/10/03)
(Chemical Equation Presented) Cucurbit[8]uril and γ-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.
