A cascade thermal isomerisation of cyclobutane di-(carbomethoxy) Δ2-1,2,3-triazolines with intramolecular 1,3-dipolar cycloreversion as the key step
作者： Davor Margetić , Ronald N. Warrener , Douglas N. Butler , Chuan-Ming Jin
DOI: 10.1016/J.TET.2012.02.073
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摘要: Abstract Unprecedented thermal isomerisation of the strained Δ2-1,2,3-triazolines led to formation products possessing a novel 1,2,7-triaza-[3.3.0]octa-2-ene ring system incorporated in norbornane framework. Experimental evidence and quantum chemical calculations have been used support postulated reaction mechanism involving as first step, rare example intramolecular 1,3-dipolar cycloreversion. Subsequently, several steps closure, hydrogen shifts an addition are leading observed product this deep-seated isomerisation. The influence changing substituents on outcome cascade was also studied.
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