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New method for in situ generation of enolate-iminium 1,4-dipoles for [4 + 2] and [4 + 1] dipolar heterocycloaddition reactions
Zhulanov, Vladimir E. Dmitriev, Maksim V. Maslivets, Andrey N. Rubin, Michael
Zhulanov, Vladimir E.
Dmitriev, Maksim V.
Maslivets, Andrey N.
Rubin, Michael
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Abstract
Generation of hydrazoylketenes by thermal decomposition of N-(diphenylenamino)pyrrolediones is accompanied by 5-exo-trig ring closure to furnish a zwitterionic dihydropyrazolone species. In contrast to Lisowskaya's earlier report, we established that in most cycloaddition reactions such dihydropyrazolones react as 1,4-dipoles. This reactivity pattern was demonstrated in several [4 + 4]-homodimerizations and in a series of [4 + 2] and [4 + 1] cycloaddition reactions with various dipolarophiles.
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2016-09-14
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Royal Society of Chemistry
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Zhulanov_RSC_2016.pdf
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Zhulanov, V. E., Dmitriev, M. V., Maslivets, A. N., & Rubin, M. (2016). New method for in situ generation of enolate-iminium 1,4-dipoles for [4 2] and [4 1] dipolar heterocycloaddition reactions. RSC Advances, 6(93), 90239-90247. doi:10.1039/c6ra21981k