Regio- and exo-π-facial selective 1,3-dipolar cycloaddition of α-(3-pyridyl)-N-phenylnitrone to norbornadiene: activation of a π-bond of norbornadiene and control of regiochemistry of nitrone cycloaddition by nitrone addition to the other double bond

Paul Singh Ishar, Mohan ; Singh, Gurpinder ; Elango, Munusamy ; Subramaniam, Venkatesan (2006) Regio- and exo-π-facial selective 1,3-dipolar cycloaddition of α-(3-pyridyl)-N-phenylnitrone to norbornadiene: activation of a π-bond of norbornadiene and control of regiochemistry of nitrone cycloaddition by nitrone addition to the other double bond Heterocycles, 68 (7). pp. 1409-1419. ISSN 0385-5414

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Related URL: http://dx.doi.org/10.3987/COM-06-10732

Abstract

Thermal cycloaddition of α-(3-pyridyl)-N-phenylnitrone to a π-bond in norbornadiene not only activates the other double bond towards 1,3-dipolar cycloaddition, it also regulates the regiochemistry of addition leading to regio- and exo-π-facial selective formation of novel 2:1 cycloadducts. A DFT analysis in terms of the global and local reactivity indices affords a rationalization of the obtained results.

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