A NOVEL SYNTHESIS OF PHOSPHORUS HETEROCYCLES. REACTION OF α -HYDRAZIDOYL HALIDES WITH PHOSPHORANES AND LAWESSON'S REAGENT

Abstract

Hydrazidoyl halides 1a reacted with diethylphosphonoacetonitrile (2a) in sodium ethoxide to yield the hydrazine derivative 4a which readily cyclized to form the corresponding diazaphosphole 5 . The latter was hydrolyzed to form the final product 6, with the formation of a low yield of a second product 7a . Similarly 1b, c reacted with diethylphosphonoacetonitrile and triethylphosphonoacetate 2a, b to produce the corresponding diazaphospholes 6b–d . Interaction of hydrazidoyl halides 1b, d–g with Lawesson's reagent in dry toluene produced 1,3,4-thiadiazaphosphole derivatives 10b, d, e and 11f, g respectively.

Keywords:

• Hydrazidoyl halides
• phospholes
• phosphoranes
• Lawesson's reagent (LR)
• diazaphospholes