Intramolecular Ketenimine−Ketenimine [2 + 2] and [4 + 2] Cycloadditions

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 funct...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-07, Vol.72 (15), p.5863-5866
Main Authors: Alajarín, Mateo, Bonillo, Baltasar, Sánchez-Andrada, Pilar, Vidal, Ángel, Bautista, Delia
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0704661