Intramolecular Ketenimine−Ketenimine [2 + 2] and [4 + 2] Cycloadditions
Mateo Alajarı́n, Baltasar Bonillo, Pilar Sánchez‐Andrada, Ángel Vidal, Delia Bautista
Abstract
Mateo Alajarı́n, Baltasar Bonillo, Pilar Sánchez‐Andrada, Ángel Vidal, Delia Bautista
Abstract
Bis(ketenimines), in which the two heterocumulenic functions are placed in close proximity on a carbon skeleton to allow their mutual interaction, show a rich and not easily predictable chemistry. Intramolecular [2 + 2] or [4 + 2] cycloadditions are, respectively, observed when both ketenimine functions are supported on either ortho-benzylic or 2,2'-biphenylenic scaffolds. In addition, nitrogen-to-carbon [1,3] and [1,5] shifts of arylmethyl groups in N-arylmethyl-C,C-diphenyl ketenimines are also disclosed.
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Bis(ketenimines), in which the two heterocumulenic functions are placed in close proximity on a carbon skeleton to allow their mutual interaction, show a rich and not easily predictable chemistry. Intramolecular [2 + 2] or [4 + 2] cycloadditions are, respectively, observed when both ketenimine functions are supported on either ortho-benzylic or 2,2'-biphenylenic scaffolds. In addition, nitrogen-to-carbon [1,3] and [1,5] shifts of arylmethyl groups in N-arylmethyl-C,C-diphenyl ketenimines are also disclosed.
Key concepts: Ketenimine, Intramolecular force, Chemistry, Carbon fibers, Nitrogen, Stereochemistry, Computational chemistry, Organic chemistry