216171-28-7Relevant articles and documents
The reaction of N-magnesium derivatives of pyrroles with N- mesylchloromethylpyrroles: A synthesis of dipyrrylmethanes
Abell, Andrew D.,Nabbs, Brent K.,Battersby, Alan R.
, p. 8163 - 8169 (1998)
Attachment of an alkyl- or arylsulfonyl group at the nitrogen atom of a pyrrole reduces the aromaticity and electron availability of the system. This is confirmed by the structure of an N-tosylated chloromethylpyrrole determined by X-ray crystallography. In agreement, N-mesylated chloromethylpyrroles are handleable materials which react smoothly with N- magnesium derivatives of pyrroles to provide a novel route for synthesis of dipyrrylmethanes. Several examples of this synthesis are described, including the construction of molecules carrying deuterium at the interpyrrolic methylene group.
