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Updated: Jun 24, 2025

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Nitrile Imine Cyclizations and Rearrangements: N-Phenyl-C-styrylnitrile Imine and N-Phenyl-C-phenylethynylnitrile

Maryam Miri1, Avat Arman Taherpour1, Curt Wentrup2

  • 1Department of Organic Chemistry, Faculty of Chemistry, Razi University, Kermanshah 67149-67346, Iran.

The Journal of Organic Chemistry
|June 13, 2024
PubMed

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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