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Firsan, Sharbil Jurji 2014-12-15T23:18:39Z 2014-12-15T23:18:39Z 10000-01-01 1986 1986 Two N,O-dialkylacetimidate N-oxides and their hydrochlorides, and the hydrochloride of O-ethyl-N-methylpropionimidate N-oxide were prepared in dichloromethane solutions by the acid-catalyzed condensation of N-alkylhydroxylamines with aliphatic orthoesters. The (alpha)-alkoxynitrones and their hydrochlorides were characterized by ('1)H NMR spectroscopy and, in one case, by reaction with ammonia and aniline. In addition, a series of N,S-dialkylthioimidate N-oxides hydroiodides was synthesized by S-alkylation of N-alkylthiohydroxamic acids with methyl and ethyl iodide in acetone. The free (alpha)-alkylthionitrones were liberated from the corresponding hydroiodides with sodium carbonate or bicarbonate in water. The thioimidate N-oxides and their hydroiodides were characterized spectroscopically and their equilibrium ratios were determined in bromobenzene and acetone, respectively. The E/Z stereochemistry of the C-phenyl thioester nitrones is unambiguously established on the basis of an X-ray structural analysis on the N,S-dimethyl compound, and that of the C-alkyl counterparts is tentatively assigned on the basis of long range coupling, nuclear Overhauser effects, and chemical shift correlations. The reactions of (Z)-N,S-dimethylthiobenzimidate N-oxide, with methylmagnesium bromide and aqueous acid and base were investigated. Made available in DSpace on 2014-12-15T23:18:39Z (GMT). No. of bitstreams: 1 8623296.pdf: 6221652 bytes, checksum: e6b607842195fdfa68a65ea6f759c91d (MD5) Previous issue date: 1986 Embargo set by: Seth Robbins for item 70490 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 185 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1986. http://hdl.handle.net/2142/70324 (UMI)AAI8623296 Chemistry, Organic Acyclic Imidate and Thiomidate Normal-Oxides: Nitrones of Esters and Thioesters (alpha-Alkoxynitrones, Alpha-Alkylthionitrones, Normal - Alkylthiohydroxamic Acids, X-Ray) text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.