Phosphorylation of N‐iso‐propyl‐ and N‐tert‐butylpyrroles with phosphorus(III) halides

Phosphorylation of N‐Silylpyrroles with Phosphorus Tribromide

“…Phosphorylation selectivity is caused by bulky trialkylsilyl substituents, as was the case with N-tert-butylpyrrole [5].…”

“…To exemplify, Ntrimethylsilylpyrrole is practically unreactive toward phosphorus halides in benzene, in contrast to Ntert-butylpyrrole that is readily phosphorylated with phosphorus tribromide in benzene, so that the reaction goes to completion within 12 h [5]. NTrialkylsilylpyrroles are much more difficult to phosphorylate with phosphorus trichloride, a weaker electrophile as compared to phosphorus tribromide.…”

“…NTrialkylsilylpyrroles are much more difficult to phosphorylate with phosphorus trichloride, a weaker electrophile as compared to phosphorus tribromide. For instance, N-trimethylsilylpyrrole is phosphorylated with PCl 3 in pyridine to a degree of 20% after a 24-h reaction time, whereas the phosphorylation of N-tert-butylpyrrole under the same conditions goes to completion within this period [5].…”

A Simple Approach to Vicinal Pyrrolylphosphane Aldehydes

“…Phosphanylation of N ‐alkyl pyrroles with R 2 PX proceeds either at 2‐ or at 3‐ position depending on substituents at the phosphorus and at the pyrrole nitrogen atoms . The analysis of NMR spectra of 4c did not provide a clear confirmation of its constitution.…”

Facile synthesis and nematicidal activity evaluation of thiophosphinyl amide [(Pz)2P(S)NHR] and thiophosphonyl diamide [(Pz)P(S)(NHR)2] (Pz = 1,3,5-trimethylpyrazole, R = biphenyl derivatives)

“…A C-5 methyl group should prevent migration of a phosphine group between C-2 and C-3, a process that has been widely observed for other pyrazole derivatives. 36,37 In addition, some analogues of 2-aminobiphenyl have been employed as pesticidal agents.…”