Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 29, Pages 5637-5653Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200383
Keywords
Reaction mechanisms; Cyclo-addition; Electrocyclization; Sigmatropic rearrangement; Radicals; Biradical -cyclization; Cumulenes; Ketenimines
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Funding
- Ministerio de Economia y Competitividad of Spain [CTQ2008-05827/BQU]
- Fundacion Seneca-CARM [08661/PI/08]
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Selected recent developments in the chemistry of ketenimines are presented, demonstrating that heterocumulenes of this class are versatile reactive intermediates in the synthesis of nitrogenated heterocycles. This microreview includes examples of intramolecular nucleophilic and radical additions, biradical cyclizations, 4p- and 6p-electrocyclic ring closures, [2+2], [3+2] and [4+2] cycloadditions, ketenimine-to-nitrile rearrangements and 1,3-X, 1,5-X and 1,5-H shifts.
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