Accession Number:

AD0261707

Title:

FACTORS AFFECTING THE POSITION OF ALKYLATION OF ALKALI METAL SALTS OF PYRROLE WITH ALLYLIC HALIDES

Descriptive Note:

Corporate Author:

KANSAS UNIV LAWRENCE

Personal Author(s):

Report Date:

1961-03-13

Pagination or Media Count:

1.0

Abstract:

The reaction of alkali-metal salts of pyrrole with allyl, crotyl and benzyl halides affords a mixture of the 1- and 2-substituted pyrroles, along with varying amounts of disubstituted pyrroles. It has been found that the product ratio of the two monosubstituted pyrrole isomers in each case is affected markedly by the nature of the medium and of the metal ion. In general, the percentage of alkylation at the nitrogen atom 1-position increases with the solvating power of the medium and decreases with the coordinating ability of the metal ion. These effects are explained on the basis that dissociation of the pyrryl-metal ion pair favors nitrogen alkylation. It has been shown that disubstituted pyrroles arise only from 2-alkylated pyrroles by further alkylation. Author

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Distribution Statement:

APPROVED FOR PUBLIC RELEASE