Laboratoire des Interactions Moléculaires et Réactivité Chimique et Photochimique
UMR 5623

Seminar by Pr Yuriy Shermolovich / Laboratory of organosulfur compounds - Institute of organic chemistry / Kiev - Ukraine

Monday 28th of May 2018 - 2pm - Maroni room / MHT

Pr Yuriy Shermolovich, researcher at the Laboratory of organosulfur compounds in Kiev, is hosted by the IMRCP for 1 month. He will give a talk about: Sulfur containing reagents for fluorinated heterocycles synthesis

The presentation concerns first the synthetic possibilities of simple 1,1-dihydropolyfluoroalkyl sulfides RfCH2SR, sulfones RfCH2SO2R and fluorinated thiocarboxylic acid derivatives. Dithioesters and thioamides, RfCSSR and RfCSNR2, are used to prepare different fluorinated heterocyclic compounds such as: 1,2,3-triazoles, pyrazoles, imidazoles, thiazoles, uracils, pyrimidines, thiopyranes, dihydrithiopyranes, oxathiines, tetrathiafulvalenes.
A series of chiral S- or O-alkyl thionoesters have been synthesized by treatment of trifluorothioacetyl- or 2,2,3,3-tetrafluorothiopropionyl chloride with corresponding thiols or alcohols. The thia-Diels-Alder reaction of the thionoesters with symmetrical 1,3-dienes proceeds with diastereoselectivity up to 60%. Structures of cycloaddition products and corresponding transition states have been studied at the DFT level of approximation. The experimentally observed diastereomeric excess has been referred to differences in activation energies of transition states, preceding formation of the diastereomeric cycloaducts.

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