Charge-cumulated hetarenes —1. (Pyrimidin-2,4,6-triyl)-tris-hetarenium salts

✍ Scribed by Andreas Schmidt; Annemarie Hetzheim

• Book ID: 104207416
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 322 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01039-3

✦ Synopsis

Nucleophilic substitution on 2,4,6-trichloropyrimidine (1) with 4-dimethylaminopyfidine, 1-methylimidazole and 4-(pyrrolidin-1-yl)pyridine forms the (pyrimidin-2,4,6-triyl)-tris-hetarenium salts 3, 4 and 5, respectively. Whereas the chlorides 3a, 4a, and 5a are hygroscopic, stabilization can be achieved by tetraphenylborate (3b, 4b, 5b) or iodide (3¢, 4e, 5c) as gegenion. Due to the formation of charge-transfer complexes, the iodides exhibit an effect of negative solvatochromism