For many decades, phosphorus oxychloride (POCl3) has been a workhorse dehydrating agent in the synthesis of organic isocyanides from the corresponding formamides. In 2011, Kitano and coworkers suggested a new method for accessing certain benzenoid aryl and alkyl isocyanides by employing substantially less toxic chlorophosphate derivatives to dehydrate N-formamides. We have expanded the scope of this new synthetic protocol by replacing POCl3 with ethyl and/or phenyl dichlorophosphates in the syntheses of various isocyanoazulene ligands recently introduced by the Barybin laboratory. The benefits and limitations of dichlorophosphate reagents in the preparation of nonbenzenoid isocyanoarenes will be discussed in detail.

Syntheses of isocyanoazulenes via dehydration of the corresponding N-formamidoazulenes with dichlorophosphates

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.