Chemistry of phosphorus ylides: Part 45 synthesis of phosphoranylidene, thietane, azetidine and thiazinane derivatives as potent chemo preventative agents

GRAPHICAL ABSTRACT

ABSTRACT

Reactions of nucleophilic active phosphacumulenes with iso(thio)cyanate compounds were performed. The reaction products depend on the nature of the reagent, substrate and the condition of the reaction used. New heterocyclic 4-membered or 6-membered sulfur and nitrogen compounds such as phosphoranylidene thietane, azetidine and thiazinane were obtained. On the other hand, the stable phosphonium ylides with the iso(thio)cyanate afforded phosphoranylidene thiocarbamoyl derivatives. Possible reaction mechanisms are considered and the structural assignments are based on compatible analytical and spectroscopic data.

KEYWORDS:

• Isothiocyanates
• isocyanate
• ylides
• phosphoranylidene
• thietane
• azetidine
• thiazinane
• thiocarbamoyls