SYNTHESIS, SPECTRAL CHARACTERISTICS AND STRUCTURE OF 1,3-DISUBSTITUTED TETRAZOLINONES AND 1,4-DISUBSTITUTED TETRAZOLINONES

Reaction of ethylene oxide with 1-alkyl- or 1-aryl-1,4-dihydrotetrazole-5-thiones in acetic acid affords the corresponding mesoionic 1-alkyl- or 1-aryl-3-(2-hydroxyethyl)-tetrazolium-5-olates 4-6. The X-ray structure of one of these compounds (5) is presented. On the other hand, the reaction of tetrazolinones with 2-chloroethanol in the presence of potassium hydroxide affords a mixture of the corresponding 1,3- and 1,4-disubstituted isomers. The isomers can be distinguished easily by their IR, H-1 or C-13 NMR spectra. The fragmentation of these compounds in the mass spectrometer is discussed.