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Title: Interplay of dual reactivity in the reaction of pentafulvenes with 1,2,4-triazoline-3,5-diones: Experimental and theoretical investigations
Authors: Anas, S
Syam Krishnan, K
Sajisha, V S
Anju, K S
Radhakrishnan, K V
Suresh, E
Suresh, C H
Keywords: Diels-alder reactions
Effective core potentials
6+3 cycloaddition
Diastereofacial reactivity
3-oxidopyrylium betaine
Molecular calculations
Facile synthesis
Issue Date: 2007
Publisher: Royal Society of Chemistry
Citation: New Journal of Chemistry 31(2):237-246;Feb 2007
Abstract: A detailed investigation on the reaction of pentafulvenes with N-substituted-1,2,4-triazoline-3,5-diones leading to the formation of five- and seven-membered azapolycycles is described. The observed reactivity is explained based on the electronic and frontier molecular orbital features of pentafulvene and triazoline dione, which suggested that the latter molecule can add to the former one via a [4 + 2] cycloaddition or it can undergo a nucleophilic reaction at the exo carbon atom of pentafulvene. These reactions would ultimately give the same product and the energetics of them suggested that both mechanisms are operative in the reaction conditions.
ISSN: 1144-0546
Appears in Collections:2007

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