Intramolecular 1, 3-dipolar Cycloreversion - the Key Step in Thermal Isomerisations of Cyclobutane Di-(carbomethoxy) Triazolines (CROSBI ID 505339)
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Podaci o odgovornosti
Margetić, Davor ; Jin, C.-M. ; Warrener, Ronald N. ; Butler, Doug N.
engleski
Intramolecular 1, 3-dipolar Cycloreversion - the Key Step in Thermal Isomerisations of Cyclobutane Di-(carbomethoxy) Triazolines
Thermal isomerisation of the strained cyclobutane diester triazoline led to the formation of the product 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 (semiempirical and DFT) 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, [1, 3]hydrogen-shifts and an intramolecular addition are postulated leading to the observed product of this deep-seated isomerization. The influence of changing substituents on the product outcome of this novel reaction cascade was also studied.
triazolines; dipolar cycloadditions
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Podaci o prilogu
2004.
objavljeno
Podaci o matičnoj publikaciji
Book of abstracts / 15th International Conference on Organic Synthesis, ICOS-15
Nagoya:
Podaci o skupu
15th International Conference on Organic Synthesis, ICOS-15
poster
01.08.2004-06.08.2004
Nagoya, Japan