ChemInform Abstract: Phosphorus Containing Enamines. Part 4. Reaction of Alkyl and Phenyl Substituted N‐Vinylpyrroles with Phosphorus Pentachloride.

Abstract

Das N‐Vinyl‐octahydrocarbazol (I) reagiert mit Phosphorpentachlorid unter starker Harzbildung zu dem Hexachlorophosphat (II), das mit Schwefeldioxid in das Phosphonsäurechlorid (III) übergeht.

Organophosphorus Azoles Incorporating a Tetra-, Penta-, and Hexacoordinated Phosphorus Atom: NMR Spectroscopy and Quantum Chemistry

“…17). The reaction of the salts 53-55 and triethylamine proceeds via the elimination of hydrogen chloride to give rise the corresponding phosphol-2-enes 59, 60, the structure of which was confirmed by 1 H, 13 C and 31 P NMR spectroscopy data [61].…”

“…1-vinylpyrroles and their annulated analogs, indoles and carbazoles have also been phosphorylated by the reaction with phosphorus pentachloride to provide various phosphorylation products both at the vinyl group and at the pyrrole cycle [ 60 , 61 , 62 , 63 ]. The introduction of a phosphorus-containing fragment into the pyrrole rings is a structural motif of bioactive natural products and pharmaceutical drugs [ 64 , 65 , 66 , 67 ].…”

“…The phosphorylation of N -vinylpyrroles which do not contain strong electron-withdrawing groups in the ring, as well as their annulated analogues, N -vinylindole and N -vinylcarbazole, has been studied [ 61 ]. The interaction of these pyrroles with phosphorus pentachloride yields various products of phosphorylation both at the pyrrole ring and at the vinyl group ( Scheme 13 , Table 17 ).…”

“…Hexachlorophosphates 53 – 55 after the action of SO 2, are converted into the corresponding pyrrolo [1,2-a]-1oxo-1,3-dichloro-4,1-azaphospholanes 56 – 58 ( Table 17 ). The reaction of the salts 53 – 55 and triethylamine proceeds via the elimination of hydrogen chloride to give rise the corresponding phosphol-2-enes 59 , 60 , the structure of which was confirmed by 1 H, 13 C and 31 P NMR spectroscopy data [ 61 ].…”

“…The phosphorylation of indoles and carbazoles occurs exclusively at the vinyl group, as evidenced by the NMR data [ 61 ]. The indole and carbazole fragments of the latter are not attacked by phosphorus pentachloride ( Scheme 14 ).…”