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ChemInform Abstract: Regioselective Reactions of Ambident Dianions. Part 5. Domino Reaction of Lithiated Allenes with Nitriles.

✍ Scribed by P. LANGER; M. DOERING; D. SEYFERTH

Book ID: 101879132
Publisher: John Wiley and Sons
Year: 2010
Weight: 28 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199901132

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✦ Synopsis

Regioselective Reactions of Ambident Dianions. Part 5. Domino Reaction of Lithiated Allenes with Nitriles.

-Addition of nitriles to dilithiated allenes results in a unique domino cyclization, which involves the so far highest number of nitrile molecules added to an organolithium reagent, providing sterically crowded imidazoles. A plausible reaction mechanism is pro-

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## Abstract Critical to this reaction is the development of a biphasic system for base‐induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base‐sensitive dipolarophile.