ChemInform Abstract: Stereo- and Regioselective Cycloaddition of Norbornene to 2,4,6-Triazidopyridines.

✍ Scribed by S. V. CHAPYSHEV; V. M. ANISIMOV

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199822100

✦ Synopsis

Stereo-and Regioselective Cycloaddition of Norbornene to 2,4,6-Triazidopyridines.

-The reaction of 3-cyano-and 3-chloro-2,4,6triazidopyridines (I) and (V) with one equivalent of norbornene (II) proceeds regio-and stereoselectively to afford the 4-exo-azatricyclooctyl pyridines (III) and (VI) respectively. While the 3-cyano derivative (I) reacts smoothly with excess norbornene to give the 2,4,6-tris(exo-azatricyclooctyl)pyridine (IV), the reactivity of the 3-chloro analogue (VI) towards further addition is reduced. Thus, the use of rhodium or copper catalysts or an enhanced temperature is necessary for the further addition giving the tris(exoazatricyclooctyl)pyridine (VII).