Electrolytic methoxylation of 3,4-bis(hydroxymethyl) furan and synthesis of 4,5-bis-(hydroxymethyl) pyridazine

3,4-Bis(hydroxymethyl)furan was electrolytically methoxylated during intense cooling. 4,5-Bis(hydroxymethyl)pyridazine was obtained by reaction of the methoxylation product — 2,5-dimethoxy-3,4-bis (hydroxymethyl)-2,5-dihydrofuran — with hydrazine hydrate.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1306–1307, October, 1970.     

Reaction of 2-chloro-5-methylbenzoquinone with Β-aminocrotonic ester derivatives

The reaction of 2-chloro-5-methylbenzoquinone with -aminocrotonic ester derivatives was studied by PMR spectroscopy in CD₃COOD. The spectra indicate the formation of intermediate hydroquinone and quinone derivatives, which subsequently transform into the corresponding indoles. It was shown that the indolization proceeds unequivocally at the 3-position of the initial benzoquinone, and the rate of formation of the indole derivatives decreases with increase in the size of the substituent at the nitrogen atom of the -aminocrotonic ester. The starting, intermediate compounds and the end products observed in the PMR spectra were identified by comparison with specially synthesized compounds.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 324–328, March, 1990.     

Electronic regioselectivity in the reactions of pyridinium ylides with tetracyanoethylene

Highly regioselective reactions of pyridinium ylides with tetracyanoethylene occur via an Ad_N-E mechanism to form Z-isomers of 3-aroyl-3-(1-pyridinio)-1,1,2-tricyano-2-propenides-1, corresponding in structure to 1,4-ylides with maximum charge separation. If the unsaturated nitrite starting material contains a nucleofugal group 1,2-elimination predominates over 1,3-elimination.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1087–1094, August, 1991.