Synthesis, Spectral Characteristics and Structure of 1,3- and 1,4-Disubstituted Tetrazolinones

Article abstract of DOI:10.1002/prac.199533701136

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, 1H or 13C NMR spectra.The fragmentation of these compounds in the mass spectrometer is discussed.