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Communication | Regular issue | Vol 36, No. 1, 1993, pp.33-36
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6205
On the Regioselectivity in the Hurd-Mori Reaction

Mikako Fujita, Takeo Kobori,* Tamejiro Hiyama, and Kiyoshi Kondo

*Sagami Central Research Center, 4-4-1 Nishi-Ohnuma, Sagamihara, Kanagawa 229-0012, Japan


Various α-substituted (Y) acetone hydrazones were subjected to the Hurd-Mori reaction to give the 4-methyl-5-Y-substituted 1,2,3-thiadiazoles and/ or 4-Y-CH2 derivatives. The ratio of the two products changed drastically depending on the kind of the substituent Y and was parallel to the relative rate of enolization of the two α-carbons in the parent ketones.