Phosphaalkyne
In chemistry, a phosphaalkyne (IUPAC name: alkylidynephosphane) is an organophosphorus compound containing a triple bond between phosphorus and carbon with the general formula R-C≡P. Phosphaalkynes are the heavier congeners of nitriles, though, due to the similar electronegativities of phosphorus and carbon, possess reactivity patterns reminiscent of alkynes. Due to their high reactivity, phosphaalkynes are not found naturally on earth, but the simplest phosphaalkyne, phosphaethyne (H-C≡P) has been observed in the interstellar medium. Synthesis From phosphine gas The first of preparation of a phosphaalkyne was achieved in 1961 when Thurman Gier produced phosphaethyne by passing phosphine gas at low pressure over an electric arc produced between two carbon electrodes. Condensation of the gaseous products in a –196 °C (–321 °F) trap revealed that the reaction had produced acetylene, ethylene, phosphaethyne, which was identified by infrared spectroscopy. By elimination reactions Elimination of hydrogen halides Following the initial synthesis of phosphaethyne, it was realized that the same compound can be prepared more expeditiously via the flash pyrolysis of methyldichlorophosphine (CH3PCl2), resulting in the loss of two equivalents of hydrogen chloride. This methodology has been utilized to synthesize numerous substituted phosphaalkynes, including the methyl, vinyl, chloride, and fluoride derivatives. Fluoromethylidynephosphane (F-C≡P) can also be