39502-94-8

Upstream product

• 700-12-9 pentamethylbenzene, 
• 16652-64-5 O-benzyl-S-tyrosine 
• 87-85-4 Hexamethylbenzene 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 100-51-6 benzyl alcohol 
• 538-86-3 benzyl methyl ether 
• 7285-83-8 2,4,6-tris(benzyloxy)-1,3,5-triazine 

Downstream Products

• 85296-43-1 2,3,4,5,6-pentamethyl-4'-nitrodiphenylmethane 

Relevant academic research and scientific papers

Making photochemically generated phenyl cations visible by addition to aromatics: Production of phenylcyclohexadienyl cations and their reactions with bases/nucleophiles

The benzenediazonium cation and its 4-fluoro, 4-chloro, 4-bromo, 4- methyl, and 4-methoxy derivatives were photolyzed in 1,1,1,3,3,3- hexafluoroisopropyl alcohol (HFIP) with 20-ns pulses of 308-nm light from a XeCl excimer laser. This leads to a pronounced and permanent depletion of the parent compounds (quantum yields 0.89-0.96), but no signal from a transient is seen. However, on addition of aromatics such as, e.g., mesitylene, strong signals due to species with λ(max) at 250-260 and 350-390 nm are detected. In the absence of bases/nucleophiles other than the aromatics, these species, which do not react with oxygen, have a lifetime in the microsecond to millisecond range. On the basis of their absorption spectra and their reactivity with typical bases/nucleophiles such as halides, alcohols, and ethers, the transients are identified as cyclohexadienyl cations formed from the photoproduced 'invisible' phenyl cations by addition to the ring of the added aromatics. On the basis of competition data for reaction with HFIP and aromatic, the substituents Me, MeO, and Cl lead to a weak increase in selectivity of the phenyl cation, whereas F and Br do not influence the selectivity.

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Triazine-Based Cationic Leaving Group: Synergistic Driving Forces for Rapid Formation of Carbocation Species

A new triazine-based cationic leaving group has been developed for the acid-catalyzed alkylation of O- and C-nucleophiles. There are two synergistic driving forces, namely, stable C=O bond formation and charge-charge repulsive effects, involved in the rapid generation of the carbocation species in the presence of trifluoromethanesulfonic acid (～200 mol %). Considerable rate acceleration of benzylation, allylation, and p-nitrobenzylation was observed as compared to the reactions with less than 100 mol % of the acid catalyst. The triazine-based leaving group showed superior p-nitrobenzylation yield and stability in comparison to common leaving groups, trichloroacetimidate and bromide. A plausible reaction mechanism (the cationic leaving group pathway) was proposed on the basis of mechanistic and kinetic studies, NMR experiments, and calculations.

Development of a new benzylating reagent spontaneously releasing benzyl cation equivalents at room temperature

A new O-benzylating reagent, that is, 4-(4,6-diphenoxy-1,3,5-triazin-2-yl)-4-benzylmorpholinium trifluoromethanesulfonate (DPT-BM), has been developed. Benzyl cation equivalents are generated from DPT-BM by dissolving the compound in a solvent at room tem

A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure

Formal trimerization of the smallest unit of benzyl imidate leads to 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT), which can be used as an acid-catalyzed O-benzylating reagent. The reaction of various functionalized alcohols with 0.4 equiv of TriBOT in the presence of trifluoromethanesulfonic acid afforded the benzyl ethers in good yields. TriBOT is an inexpensive stable crystalline solid with high atom economy.

A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure

Formal trimerization of the smallest unit of benzyl imidate leads to 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT), which can be used as an acid-catalyzed O-benzylating reagent. The reaction of various functionalized alcohols with 0.4 equiv of TriBOT in the presence of trifluoromethanesulfonic acid afforded the benzyl ethers in good yields. TriBOT is an inexpensive stable crystalline solid with high atom economy.

Benzylation of arenes through FeCl3-catalyzed Friedel-Crafts reaction via C-O activation of benzyl ether

Various benzyl ethers were converted to benzyl arenes via a FeCl3-catalyzed Friedel-Crafts alkylation reaction under mild condition in good yields. This method also offered a simple and practical approach to synthesize di- or tri-aryl methanes and aryl heteroaryl methanes through the activation of C-O bonds.

An efficient synthesis of unsymmetrical diarylmethanes from the dehydration of arenes with benzyl alcohols using InCl3·4H2O/acetylacetone catalyst system

An efficient and practical synthesis of unsymmetrical diarylmethanes has been achieved from the dehydration of arenes with benzyl alcohols in the presence of catalytic amount of InCl3·4H2O/acetylacetone.

Promoting Effect of Pentamethylbenzene on the Deprotection of O-Benzyltyrosine and Nε-Benzyloxycarbonyllysine with Trifluoroacetic Acid

O-Benzyltyrosine was rapidly deprotected without formation of 3-benzyltyrosine by treatment with trifluoroacetic acid containing pentamethylbenzene.This method was also found to be useful in the deprotection of Nε-benzyloxycarbonyllysine Lys(Z