Publication: The Elusive 1,4-Diazabutatrienes: Lurking in the Shadows
Authors
Marin-Luna, Marta ; Alajarín, Mateo
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DOI
10.1002/ejoc.202000518
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info:eu-repo/semantics/article
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Abstract
Isocyanides are isomers of cyanides in which its terminal carbon atom can exist in a divalent state. Their ambivalent electronic nature as nucleophile or electrophile and wide reactivity turn the isocyanide scaffold in a valuable synthon for the synthesis of structurally complex molecules, in particular azacycles. Although they are known to polymerize easily, the dimerization of isocyanides affording head-to-head dimers, namely 1,4-diazabutatrienes R1-N=C=C=N-R1, has been scarcely explored. Nowadays the experimental isolation of this kind of heterocumulenes is still a challenge. In this minireview, covering a period of sixty years, we highlight the role of 1,4-diazabutatienes as putative reaction intermediates in the homo- and heterodimerization of different types of isocyanides. Added to this, we revise a set of reported reactions in which the formation of a transient 1,4-diazabutatriene intermediate has not been proposed but could be considered as a plausible alternative.
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Citation
European Journal of Organic Chemistry, 2020, 2020, 5496 - 5500
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