Synthesis Stereochemistry And Dynamic Behavioi Of Some Thioacrylamides

The reaction of W,N-Dimethylamides with the dimer ofrnp-methoxyphenyl thionophosphine sulfide (Lawesson,' s reagent)rngives N,N-Dimethylthioamides. BY treating these disubsti ...rntuted thioamides with (i) the Vilsmeir -'Haack Arnoldrncomplex (formamide chloride) and (ii) Bis-(dimethylamino)tert-rnbutoxy methane, mode1compounds (Me2N-CHPO(R)~~-NR2)rn",ere synthesized. Substitution reactions '1ere also carried:rnout using these model compounds (3-aminothioacrylamides) orrntheir imi.nium salts with a primary amine (p-anisidine) to:rnsynthesize the corresponding 3-anisidinothioacrylamides.rnThe reactions were successful and yields ~ere nearlyrnquantitative.rnThe dynamic behaviour and the groUQdstate stereochemistryrnof these model compounds have been studied. Based on 1H_NMRrnstudy and LIS investigation, rotational barriers as well as'rnthe preferred conformation of some of these model compoundsrnhave been determined from the proposed three dimensiona:trngeometries

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