ChemInform Abstract: New p‐Dimethylaminophenyldichlorophosphine Derivatives.

Abstract

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C‐Phosphorylated pyrazoles. Reaction of N‐methyl‐ and N‐phenylpyrazoles with phosphorus(III) halides

“…When a mixture of 1,3,5-trimethylpyrazoIe and phosphorus tribromide in a 3 : 1 molar ratio was allowed to stand for 3 months, the 31P NMR spectrum of the reaction mixture showed a signal 6 -81 that can be attributed to a trispyrazolylphosphine, but we failed to isolate the compound.…”

“…In the next report, we shall 22a 23a 22b 2 Thus, vinylogs of ethyl esters of phosphorus(II1) acids 10 and 13 were found to undergo transformations analogous to those found in the Arbuzov reaction. Developing the indicated analogy, phosphonium salts 29 and 30 can be considered as vinylogs of Arbuzov reaction intermediates.…”

“…Recently, we have shown that electron-rich heteroaromatic compounds, such as pyrrole [l], indole [ 2 ] , furan [3], thiophene [4], and indolizine [S], as well as some aromatic compounds [ 6 ] , undergo C-phosphorylation with phosphorus (111) halides in basic medium. As a result, we have elaborated a preparative method for the synthesis of a wide range of substances having a direct phosphorus to heterocycle bond.…”

C-phosphorylation of n-methylpyrrole

“…As we reported previously, halides of trivalent phosphorus in the presence of a base can be applied as efficient reagents to phosphorylate a variety of electron-rich compounds derived from pyrrole [1], indole [2], furan [3], thiophene [4], and indolizine [5]. Among these heteroaromatics, pyrrole and indolizine are most reactive with respect to electrophiles and to phosphorus (III) halides in particular.…”

Phosphorylation of 2‐(3‐methyl‐1,3‐diazabuten‐1‐yl)‐3‐ethoxycarbonylthiophenes with phosphorus(III) halides

“…Because of the electron-donor effect of the N, N-dimethylhydrazono Correspondence to: Alexander M. Pinchuk; e-mail: hetfos@ ukrpack.net. group, thienylhydrazones are phosphorylated with phosphorus tribromide much more readily [3]. It might be expected that the electron-donor nature of the N,N-dimethylformamidino substituent in N-(thienyl-2)formamidines would also promote the course of the reaction under mild conditions, as in the phosphorylation of N-azolylformamidines [4].…”