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1,3,4-Trimethyl-2,2′-pyrromethen-5[1H]-one and its 1′-methyl derivative; Synthesis, thermal and photochemical reactivity

✍ Scribed by J. A. de Groot; J. Lugtenburg

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
400 KB
Volume
101
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Condensation of 1,3,4‐trimethyl‐1,5‐dihydro‐2__H__‐pyrrol‐2‐one, prepared in high yield from 3,4‐dimethylpyrrole, with pyrrole‐2‐carboxaldehyde and 1‐methylpyrrole‐2‐carboxaldehyde gives a mixture of Z‐ and E‐1,3,4‐trimethyl‐2,2′‐pyrromethen‐5[1__H__]‐one (7 and 8) and 1,1′,3,4‐tetramethyl‐2,2′‐pyrromethen‐5[1__H__]‐one (9 and 10), respectively. The Z and E forms both isomerise thermally upon heating in basic methanol to the same equilibrium state as is observed during the synthesis. Upon irradiation with light (λ > 360 nm), 7, 8, 9 and 10, similarly undergo Z‐E isomerisation.

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