Regioselective IED Diels-Alder Reaction of Bis-(4,6-dichloro-[1,3,5]triazin- 2-yl)-diazene with Furan and Its Molecular Mechanism

Author(s): Andrew Karkhut, Sviatoslav Polovkovych, Roman Lesyk*, Volodymyr Novikov

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 8 , 2020

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Abstract:

The reaction of bis-(4,6-dichloro-[1,3,5]triazin-2-yl)-diazene with furan proceeds with the formation of inverse electron demand Diels-Alder product with a high yield. M06 2X/6 31G(d,p) calculations show thermodynamic instability of “normal” DA reaction product and predict its [3,3] sigmatropic rearrangement to the thermodynamically more favorable formal IEDDA reaction product. The obtained NMR spectra were in good agreement with GIAO calculations and were in accordance with DFT thermochemical data that confirmed the formation of the described product. IR and UV/Vis spectral data was also obtained and discussed.

Keywords: IEDDA reaction, DFT calculations, polar Diels-Alder reaction, furan, 1, 3, 5-triazine, NMR spectra.

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Article Details

VOLUME: 17
ISSUE: 8
Year: 2020
Page: [639 - 644]
Pages: 6
DOI: 10.2174/1570178617666200210111928
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