Reductive C-alkylation
| Autor: | S. F. MacDonald, K. S. Y. Liang, D. M. Clugston, B. V. Gregorovich |
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| Rok vydání: | 1968 |
| Předmět: | |
| Zdroj: | Canadian Journal of Chemistry. 46:3291-3300 |
| ISSN: | 1480-3291 0008-4042 |
| DOI: | 10.1139/v68-545 |
| Popis: | At 95–115°, paraformaldehyde and hydriodic acid completely C-methylate aromatics such as benzene and phenol. Pyrroles are C-methylated similarly, carbethoxy and acetyl groups being lost. In hydriodic acid at 15–45°, typical pyrroles retain these groups and all free positions are C-alkylated, methylated by paraformaldehyde, or otherwise alkylated by the appropriate carbonyl compound. The alkylation of a 2-free- by a 2-formylpyrrole led to a dipyrrylmethane. With pyrroles, hydriodic acid may be replaced by another strong acid and a reducing agent. This was necessary when a β-free pyrrole gave the iodo–alkyl derivative rather than the expected product. |
| Databáze: | OpenAIRE |
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