| Co-Investigator(Kenkyū-buntansha) |
YOSHIO ASO Faculty of Engineering, Hiroshima University, Research Assistant, 工学部, 助手 (60151065)
TETSUO OTSUBO Faculty of Engineering, Hiroshima University, Associate Professor, 工学部, 助教授 (80029884)
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| Research Abstract |
Various new synthetic organic reactions were developed using organotelluriums. Under the catalytic influence of lewis acids such as BF_3・O(C<@22<@D2H<@D25@>D2)<@D22@>D2, arenetellurinic anhydrides reacted with olefins in the presence of hydroxyl functions, carbamates, and nitriles to afford oxytellurinylation, aminotellurinylation, and amidotellurinylation products, respectively. The latter two reactions were further extended to the new one-pot syntheses of 2-oxazoldinones and 2-oxazolines from olefines, respectively. These reactions proceeded in regio- and stereo-selective fashions and worked well in intramolecular processes as well as intermolecular ones. Allyltrimethylsilanes were converted to allylamines via similar tellurinylation reactions. Electrolytic oxidation of thioamides using (p-CH<@D23@>D2OC<@D26@>D2H<@D24@>D2)<@D22@>D2Te as a mediator was studied and controlled to yield nitriles or 1,2,4-thiadiazoles selectively. New cyclopropanation and alkylidenation reactions from , -unsaturated cabonyl compounds and dibromides were developed using n-Bu<@D22@>D2Te. The reactivities of PhTeH were studied extensively and the mechanism of reduction was clarified. A new complex reagent, PhTeAlBu<@D3i(/)2@>D3, was developed and its reactivities were studied. New synthetic reactions to produce -substituted- , -unsaturated cabonyl compounds from , -unsaturated carbonyl compounds were exploited utilizing this reagent.
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