Unexpected Staudinger Reaction of α-Azidophenylacetonitrile and Triphenylphosphine: Synthesis and Crystal Structure of Aminotriphenylphosphonium Salt of Phenylmalononitrile

DOI: 10.1039/c39950001387

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 1387 - 1390 (1995)

Update date:2022-08-11

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Authors:

Molina, Pedro

Lopez-Leonardo, Carmen

Llamas-Botia, Javier

Foces-Foces, Concepcion

Fernandez-Castano, Cristina

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Article abstract of DOI:10.1039/c39950001387

Staudinger reaction of α-azidophenylacetonitrile with triphenylphosphine in 1:2 molar ratio provides the triphenylphosphinazine derived from α-diazophenylacetonitrile, whereas in 2:1 molar ratio the final product is found to be the aminotriphenylphosphonium salt of phenylmalononitrile; X-ray structure analysis of this salt indicates that the anion and cation interact with one another via hydrogen bonding.

Full text of DOI:10.1039/c39950001387

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