Substituting a methyl group gives methylbenzene.

The authors note that the detailed studies of the molecular mechanisms of DNA repair pathways were made possible by using site-specifically modified oligonucleotides and that the availability of phosphoramidites to synthesize oligonucleotides with DNA lesions has contributed to the field. They illustrate the article using primarily structural studies in the following examples:

Friedel-Crafts alkylation of methylbenzene (toluene)
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At 0°C, substituting methyl groups into methylbenzene, you get a mixture of the 2-.3- and 4- isomers in the proportion 54% / 17% / 29%. That's a higher proportion of the 3- isomer than you might expect.

S., Ethyl 2-(4-phenyl-1-1,2,3-triazol-1-yl)acetate.

Mechanistic Analysis of a Suicide Inactivator of Histone Demethylase LSD1.
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, , , , , , , and , 2004. Synthesis and characterisation of aromatic ethynyl-bridged ferrocenes. Journal of Organometallic Chemistry, 689 (4), pp. 840-847.

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Unfortunately, dX is also a very insoluble nucleoside and it has proved difficult to carry out the chemistry required to make a useful phosphoramidite for incorporating dX into oligonucleotides. However, Benner’s choice of protection for dX with dual nitrophenylethyl (NPE) protecting groups (1) has proved to be the most successful to date.4 This protected dX monomer can be incorporated into oligonucleotides using conventional synthesis. The resulting oligonucleotides are cleaved and deprotected using ammonium hydroxide at room temperature with times dependent on the protecting groups on the regular bases (4 hours for UltraMild monomers, overnight for dmf-dG, and up to 36 hours for iBu-dG). After drying, the NPE protecting groups must be removed using 0.3M tetramethylguanidine/2-nitrobenzaldoxine in water dioxane (1:1) at 70 °C for 48 hours. After evaporation, the product oligonucleotide is desalted using standard techniques.

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Our synthetic route to ferrocenequinones involvedtwo-fold aldol condensation between 1,2- diformylferrocene andnaphthalene-1,4-diol or anthracene-1,4-diol, and four-fold condensationbetween 1,2-diformylferrocene and 1,4-cyclohexanedione.

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A series of aromatic ethynyl-bridged ferrocenes with the general formula Fc-CdropC-R-CdropC-Fc (Fc = ferrocenyl, R = C6H2(-p-CH3)(2) (1), C6H4-p-C6H4 (2), C5H3N (3), 9,10-C14H8 (4), C4H2S (5), (C4H2S)(2) (6) and (C4H2S)(3) (7)) has been synthesised by the reaction of ethynyl ferrocene with the appropriate dibromo-arenes. The new complexes have been characterised by spectroscopic techniques. The structures of 3 and 7 were determined via X-ray crystallography, and both show the trans-trans configuration of the two ethynyl ferrocene groups with respect to the central R group. The electronic properties of the compounds have been studied via optical spectroscopy and cyclic voltammetry. (C) 2004 Elsevier B.V. All rights reserved.