ChemInform Abstract: REACTION OF ALKOXYVINYLDICHLOROPHOSPHINES WITH PENTACHLOROPHOSPHORANE

Abstract

Das β‐Butoxyvinyl‐dichlorphosphin (I) reagiert mit (II) zum Tetrachlorphosphoranderivat (III).

C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy

“…The 3 J HH value (15-16 Hz) of vinyl protons for the studied compounds 25-42 indicates E-(PN)-isomers; i.e., when going from hexachlorophosphates (25)(26)(27)(28)(29)(30)(31)(32)(33) to the corresponding enaminophosphoric acid dichlorides (34)(35)(36)(37)(38)(39)(40)(41)(42), the configuration of the molecule does not change. The 31 P values of chemical shifts for compounds 34-42 are typical for acid chlorides of alkenylphosphonic acids and vary in the region of 33-37 ppm.…”

“…The most abundant phosphorylating agents are alkyl-, aryl-and tetrachloro(styryl) phosphoranes [14,30]. The interaction of triethylamine with organic derivatives of phosphorus pentachloride, organyltrichlorophosphonium hexachlorophosphorates, in particular, 2-ethoxyethenyltrichlorophosphonium hexachlorophosphorate, has been studied by NMR spectroscopy [31].…”

“…A reason for the formation of compound 24 is the chlorination at the multiple bond. It should be mentioned that compound 24 was obtained [30] by heating styryltetrachlorophosphorane under much harsher conditions. The replacement of the oxygen-containing ethoxy group in hexachlorophosphorate by the phenyl group containing no oxygen atoms results in the absence of styrylphosphonyl chloride in the reaction mixture.…”

10.1007/s11176-008-2006-x

“…Since the P=O group is thermodynamically very stable, there has been little work on its functionalizaton. Subsequent chlorination of the phosphoryl group with phosphorus pentachloride to increase the coordination number of phosphorus is also possible [2]. Another known process involving the phosphoryl group is the reaction with strong halogenating reagents, such as sulfur and antimony fluorides and phosphorus pentachloride [1,2], leading to dihalophosphoranes.…”

“…Thus, the reaction of phosphorus pentachloride with a cyclic phosphorus derivative, namely, 2,6-dichloro-4-phenylbenzo[e][1,2l 5 ]-oxaphosphinine 2-oxide (I) leads to chlorination of the phosphoryl group, involving consecutive formation of penta-and tetracoordinate phosphorus derivatives: 2,2,2,6-tetrachloro-4-phenylbenzo[e] [1,2]oxaphosphinine (IV) and 2,2,6-trichloro-4-phenylbenzo[e][1,2l 5 ]oxaphosphinin-2-ylium hexachlorophosphate (V).…”