Phosphorylation ofN-iso-propyl- andN-tert-butylpyrroles with phosphorus(III) halides

Autor:	Andrei A. Tolmachev, Aleksandr M. Pinchuk, Yurii V. Dmitriv, Aleksandra A. Chaikovskaya, Sergei P. Ivonin
Rok vydání:	2005
Předmět:	Phosphorus Heteroatom Substituent chemistry.chemical_element Regioselectivity Halide General Chemistry Medicinal chemistry chemistry.chemical_compound chemistry Phosphorus tribromide Phosphorylation Organic chemistry Pyrrole
Zdroj:	Heteroatom Chemistry. 16:599-604
ISSN:	1098-1071 1042-7163
DOI:	10.1002/hc.20158
Popis:	The investigation concerns the effect of a bulky substituent at the pyrrole nitrogen atom on the orientation and regioselectivity of pyrrole phosphorylation with phosphorus(III) halides. As shown, phosphorylation of N-iso-propylpyrrole with phosphorus tribromide or trichloride proceeds nonregioselectively at positions 2 and 3 but it is followed by the 2 3 migration of the dihalogenophosphine group which quantitatively yields the 3-isomer. N-tert-butylpyrrole is regioselectively phosphorylated with halogenophosphines at position 3. The tert-butyl substituent at the nitrogen atom does not preclude the binding of even two or three pyrrolyl residues to the phosphorus atom. The key compounds, 3-pyrrolyldihalogenophosphines, were isolated in a pure state, characterized and used to obtain a number of stable phosphorus(V) derivatives. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:599–604, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20158
Databáze:	OpenAIRE
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