70153-15-0

Upstream product

• 112-92-5 1-octadecanol 
• 586-75-4 4-chlorobenzoyl chloride 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 5798-75-4 Ethyl 4-bromobenzoate 

Downstream Products

• 473828-38-5 4-Trimethylsilylethinyl-benzoesaeure-n-octadecylester 
• 473828-40-9 4-Ethinyl-benzoesaeure-n-octadecylester 
• 473828-41-0 C₇₄H₉₆N₄O₄ 

Relevant academic research and scientific papers

Surface-induced selection during in situ photoswitching at the solid/liquid interface

Here we report for the first time a submolecularly resolved scanning tunneling microscopy (STM) study at the solid/liquid interface of the in situ reversible interconversion between two isomers of a diarylethene photoswitch, that is, open and closed form, self-assembled on a graphite surface. Prolonged irradiation with UV light led to the in situ irreversible formation of another isomer as by-product of the reaction, which due to its preferential physisorption accumulates at the surface. By making use of a simple yet powerful thermodynamic model we provide a quantitative description for the observed surface-induced selection of one isomeric form.

Transesterification catalyzed by iron(III) β-diketonate species

A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)3 or other iron(III) β-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric μ-alkoxy-bridged iron(III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron β-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric μ-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)2(O-n-Bu)]2 derived from the alcoholysis of Fe(dbm)3 under alkaline conditions.

Nucleophilic acyl substitutions of esters with protic nucleophiles mediated by amphoteric, oxotitanium, and vanadyl species

(Chemical Equation Presented) A diverse array of oxometallic species were examined as catalysts in nucleophilic acyl substitution (NAS) reactions of methyl (or ethyl) esters with protic nucleophiles. Among them, oxotitanium acetylacetonate (TiO(acac)2) and vanadyl chloride (VOCl 2-(THF)x) served as the most efficient and water-tolerant catalysts. Transesterifications of methyl and/or ethyl esters with functionalized (including acid- or base-sensitive) 1° and 2° alcohols can be carried out chemoselectively in refluxed toluene or xylene in a 1:1 substrate stoichiometry using 1 mol % catalyst loading. The resultant products were furnished in 85-100% yields by simple aqueous workup to remove water-soluble catalysts. The new NAS protocol is also amenable to amines and thiols in 74-91% yields, albeit with higher loading (2.5 equiv) of protic nucleophiles. Representative examples of commercial interests such as Padimate O and antioxidant additives for plastics were also examined to demonstrate their practical applications. A 1:1 adduct between TiO(acac)2 and a given 1-octadecanol was identified as (C18H37O) 2Ti(acac)2 and was responsible for its subsequent NAS of methyl esters.

Pyrido[1,2-a]pyrazines - Starting materials for regioselective ringtransformation reactions and supramolecular architectures

The easily available pyrido[1,2-a]pyrazines of type 1 are versatile building blocks for ring transformation reactions. With heterocyclic quinones such as quinoline-2,5,8-triones 4a-c, a highly regioselective [4+2]-cycloaddition reaction takes place in the