116108-67-9

Upstream product

• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 98977-48-1 (E)-3-(4-methoxyphenyl)acrylic anhydride 

Downstream Products

• 36650-62-1 dimethyl (1R*,2S*,3R*,4S*)-3,4-bis(4-methoxyphenyl)cyclobutane-1,2-dicarboxylate 

Relevant academic research and scientific papers

Template-Directed Photochemical Homodimerization and Heterodimerization Reactions of Cinnamic Acids

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

Donor-acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization

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.

Photocatalytic Systems with Flavinium Salts: From Photolyase Models to Synthetic Tool for Cyclobutane Ring Opening

Two new photocatalytic systems based on flavinium species formed in situ by protonation of riboflavin-tetraacetate (1) with triflic acid or prepared in advance via alloxazine quaternization are presented as effective tools for oxidative cyclobutane ring [2 + 2] cycloreversion using visible light. The system with 1,3-dimethyl-8-trifluoromethylalloxazinium perchlorate (2c) was found to be superior allowing an acid-free mild procedure, which results in the opening of cyclobutanes with high oxidation potential (up to 2.14 V) and/or with sensitive groups (e.g., furan) without side reactions.

Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and γ-cyclodextrin

(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.

Coerced photodimerization reaction in the solid state through amine salt formation

Photodimerization of fumaric or several γ-form trans-cinnamic acids proceeded successfully in the solid state through amine salt formation with ammonia or some aromatic heterocyclic amines (especially, imidazole). It appears that this success is due to a small size or a planar structure of the amine. A layered or a channel-type clathrate crystal structure was revealed, respectively.

Photodimerization of cinnamic acids controlled by molecular assemblies of surfactant amine N-oxides

UV irradiation of cinnamic acids 1 involving a complex with surfactant amine N-oxides (CnDAO, n = 12, 14 and 16) as vesicles in water leads to the formation of cyclodimers (i.e. β-, δ-truxinic and/or α-truxillic acids ?). Decreasing the molar ratios of 1 to CnDAO causes the vesicles to transform into rod-like micelles and the yield of the cyclodimers decreases. The addition of HCl or NaOH to aqueous solutions of 1 and CnDAO brings about sharp changes in the self-assembly structures from vesicles to micro emulsions or rod-like micelles, accompanied by a change in product distribution in the photolysis of the complex 1. Upon addition of photoinactive carboxylic acids, phenylpropionic and palmitic acids to the 1 and C16DAO system, the rod-like micelles change into vesicles by formation of a complex with C16DAO leading to the observation of a dilution effect in the photodimerization upon addition of phenylpropionic acid. However, no dilution effect is observed for the palmitic acid. This is found to be attributable to the difference in degrees of mixing of 1 with the acids in the vesicles. These results show that photodimerization of 1 incorporated in CnDAO is controlled by a variety of molecular assemblies, i.e. rod-like micelles and homogeneous or heterogeneous vesicles.

Photochemical cyclodimerization of cinnmamic acids included in surfactant amine oxides

Photocyclodimerization of unsubstituted and p-methoxy substituted cinnamic acids incorporated in micelles, vesicles or microemulsions formed by dodecyl-(C12DAO) and hexadecyl-dimethylamine oxides (C16DAO) has been studied in water. The dimerization proceeds in the vesicle much more efficiently than in the micelles with preferable formation of head-to-head dimers. The photoreactivity and the stereochemistry of cyclodimers are affected by structural change of the molecular aggregates.