221687-79-2

Upstream product

• 67-56-1 methanol 
• 221687-73-6 1-[1-p-methylphenyltelluro-2-(2,6-dimethylphenyl)-imino]-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 183367-67-1 1-p-methylphenyltelluro-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 119072-54-7 2,6-dimethylphenyl isonitrile 

Relevant academic research and scientific papers

Radical-mediated imidoylation of telluroglycosides. Insertion of isonitriles into the glycosidic carbon-tellurium bond

Telluroglycosides react with isonitriles under photo-thermal conditions to give 1-telluroimidoylglycosides. The reaction proceeds by atom transfer radical reaction to form an imidic C-Te bond, which can be substituted to a C-C bond and C-O bond under oxidative conditions.

Synthetic and theoretical studies on group-transfer imidoylation of organotellurium compounds. Remarkable reactivity of isonitriles in comparison with carbon monoxide in radical-mediated reactions

Imidoylation of organotellurium compounds with isonitriles has been investigated in conjunction with the radical-mediated Cl homologation reaction by using CO and isonitriles. Carbon-centered radicals generated photochemically or thermally from organotellurium compounds react with isonitriles in a group-transfer manner to give the corresponding imidoylated products. Organotellurium compounds have been found to serve as effective precursors of a wide variety of stabilized radicals, namely benzyl, α-alkoxy, α-amino, and acyl radicals, which take part in the imidoylation with high efficiency. The reactions are compatible with various functional groups, and can be carried out in various solvents including environmentally benign water. The reactivity of isonitriles has been compared with that of CO through competition experiments, and the results indicate that isonitriles are superior to CO as radical acceptors in reactions with stabilized radicals. The origin of the differences has been addressed in theoretical studies with density functional theory calculations using the B3LYP hybrid functional. The calculations suggest that both carbonylation and imidoylation proceed with low activation energies, and that there are virtually no differences in the kinetic sense. Instead, it indicates that thermodynamic effects, namely differences in the stability of the acyl and the imidoyl radicals, control the overall course of the reactions.