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The Synthesis of Hybrid Molecules Based on Dimers of Norbornadiene and 1,2,3‐triazole
Author(s) -
Aminov Rishat I.,
Ivanov Artemiy A.
Publication year - 2025
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202501932
Abstract The synthesis of previously undescribed azidohexacyclotetradecanes with high yields has been accomplished for the first time by the reaction of norbornadiene dimers with hydrazoic acid formed in situ by the reaction of sodium azide with sulfuric acid. It has been established that the reactions occur with the addition of HN 3 at the double bond of hexacyclic NBD dimers and with a regioselective cleavage of one three‐carbon cycle for the heptacyclic NBD dimer – binor‐S. The next step was to develop optimal conditions for the azide‐alkyne [3 + 2] cycloaddition of azides of strained polycyclic hydrocarbons and terminal alkynes containing alkyl, cycloalkyl and phenyl substituents to yield new hybrid 1,2,3‐triazole‐containing molecules. High yields of the target compounds were achieved when experiments were performed at high temperature or under microwave irradiation.
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