Formation of [beta]-(diphenylphosphoryl)pyrroles via reactions of dibromocyclobutenylphosphine oxides with aniline

1-Phenyl-2-methyl(phenyl)-4-(diphenylphosphoryl)pyrroles are obtained, unexpectedly instead of the 1-phenyl-4-methyl(phenyl)-2-(diphenylphosphoryl)pyrrole regioisomers from a series of reactions between 1,4-dibromo-2-methyl(phenyl)-4-diphenylphosphorylcyclobutenes and aniline via nucleophilic substi...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2013-03, Vol.54 (13), p.1714-1717
Main Authors: Bogachenkov, Alexander S, Ionin, Boris I, Roeschenthaler, Gerd-Volker
Format: Article
Language:English
Subjects:
Aniline
Closures
Formations
Oxides
Pyrroles
Tetrahedrons
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:1-Phenyl-2-methyl(phenyl)-4-(diphenylphosphoryl)pyrroles are obtained, unexpectedly instead of the 1-phenyl-4-methyl(phenyl)-2-(diphenylphosphoryl)pyrrole regioisomers from a series of reactions between 1,4-dibromo-2-methyl(phenyl)-4-diphenylphosphorylcyclobutenes and aniline via nucleophilic substitution accompanied by an allylic shift, subsequent retro electrocyclization and pyrrole ring closure.
ISSN:0040-4039