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

✍ Scribed by Aleksandra A. Chaikovskaya; Yurii V. Dmitriv; Sergei P. Ivonin; Aleksandr M. Pinchuk; Andrei A. Tolmachev

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
86 KB
Volume
16
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

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

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