Synthesis of 1-chloro-1,2,4,6-selenatriazines and some products of reduction

A general route to 1-chloro-1,2,4,6-selenatriazines with substuents on 3,5 positions has been developed by the reactions of N-imidoylamidines with selenium tetrachloride. The mechanism for these reactions is discussed according to the observed intermediates. At least two intermediates exist. One of the intermediates, 1,1-dichloro-3-trichloromethyl-4H-5-diisopropylphenyl-1,2,4,6-selenatriazine, was identified by 1HNMR, Mass spectroscopy and X-ray crystallography. 1-Chloro-1,2,4,6-selenatriazines were synthesized in high yield and fully characterized. Five 1-chloro-1,2,4,6-selenatriazine crystal structures were obtained. Reduction of 1-chloro-1,2,4,6-selenatriazines with triphenylamtimony immediately produced the corresponding selenatriazinyl radicals in hot acetonitrile. Pure radicals were obtained by in-situ crystallization as their dimers from reaction. Two crystal structures were obtained for 3-trifluoromethyl-5-p-tolyl-1,2,4,6-selenatriazinyl dimer and 3-trifluoromethyl-5-p-methyloxyphenyl-1,2,4,6-selenatriazinyl dimer. EPR spectroscopy measured all radicals coupling to three unique nitrogen atoms with 7 broad lines. There is no resolvable hyperfine coupling to 77Se, 37Cl/19F and phenyl protons.

Grantor dc:publisher

Lethbridge, Alta. : University of Lethbridge, Faculty of Arts and Science, 2005

Year dc:date.issued

2005

Authors dc:creator

• Zhou, Jiamin
• University of Lethbridge. Faculty of Arts and Science

Advisor dc:contributor.supervisor

• Boeré, René T.

• Dissertations, Academic
• Selenium compounds
• Heterocyclic compounds

Language dc:language.iso

en_US

Identifier

hdl:10133/295

OAI record oai:identifier

https://opus.uleth.ca/server/oai/request?verb=GetRecord&metadataPrefix=dim&identifier=oai%3Aopus.uleth.ca%3A10133%2F295