Abstract
The reactivity of a range of heterocyclic NH compounds toward cyclohexene underp-toluenesulfonic acid catalysis was surveyed. 1,2,4-Triazole (38%), carbazole (67%) and 5-phenyltetrazole (83%) gave significant amounts of addition products. 5-Phenyltetrazole reacts with a wide range of unactivated olefins, to give addition products in 65% to 90% yield. This method represents a general, preparatively useful route to 2-alkyl-5-phenyltetrazoles.
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Additional information
Submitted in honor of the 60th anniversary of Professor Édmund Lukevits.
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. Published in Geterotsiklicheskikh Soedinenii, Nos. 11–12, pp. 1520–1527, November–December, 1996. Original article submitted September 18, 1996.
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Katritzky, A.R., Qi, M. & Wells, A.P. Additions of 5-phenyltetrazole and other heterocyclic NH compounds to olefins. Chem Heterocycl Compd 32, 1305–1311 (1996). https://doi.org/10.1007/BF01169962
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DOI: https://doi.org/10.1007/BF01169962