engleski

A cascade thermal isomerisation of cyclobutane di-(carbomethoxy) D2-1, 2, 3-triazolines with intramolecular 1, 3-dipolar cycloreversion as the key step

Unprecedented thermal isomerisation of the strained D2-1, 2, 3-triazolines led to the formation of products possessing a novel 1, 2, 7-triaza-[3.3.0]octa-2-ene ring system incorporated in a norbornane framework. Experimental evidence and quantum chemical calculations have been used to support a postulated reaction mechanism involving as the first step, a rare example of intramolecular 1, 3-dipolar cycloreversion. Subsequently, several steps involving 1, 3-dipolar ring closure, hydrogen shifts and an intramolecular addition are postulated leading to the observed product of this deep-seated isomerisation. The influence of changing substituents on the product outcome of this novel reaction cascade was also studied.

reaction mechanism ; pericyclic reactions ; reactive intermediates

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