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Abstract The active phosphacumulene ylides namely, N-phenylimino- (2), 2- oxo- (4) or 2-thioxo-vinylidenetriphenyiphosphorane (6) are nucleophilic reagents which can be considered as versatile synthons for the synthesis of new heterocycles. Moreover, It is well known that Lawesson’s reagent [2,4-bis(4-methoxyphenyl)- 1 ,3,2,4-dithiaphosphetane-2,4-disulfide] (la) exisfs in equilibrium with the monomeric form (ib). This reagent is used as thionating agent and in the synthesis of heterocyclic thiophosphoryl compounds. A comparative study on the reactivity of the different phosphacumu lenes 2, 4 and 6, phosphallene 8 ylides and the iminophosphorane 10, towards Lawesson’s reagent 1, has been performed, to produce new bioactive phosphorus substances. When Lawesson’s reagent 1, was allowed to react with the active phosphacumulene ylides 2, 4 and 6, the reactions proceed by addition with cyclization to give the new four membered thiaphosphetane derivatives 3b, 5 and 7 respectively. When two moles of Lawesson’s reagent were allowed to react with one mole of (2-oxovinylidene)triphenylphosphorane (4), the same thiaphosphetanone 5 was obtained, and no thionation to the carbonyl group occured to get the thioanalogue derivative 7. |