Evidence for Ambiphilic Behavior in (CO)5W=NPh. Conversion of Carbonyl Compounds to N-Phenyl Imines via Metathesis

Bruce A. Arndtsen, Hanadi F. Sleiman, Andrew K. Chang, Lisa McElwee-White

Research output: Contribution to journalArticle

45 Scopus citations

Abstract

(CO)5W=NPh (5) has been generated in the presence of aldehydes, ketones, and thioketones and found to undergo metathesis with these substrates to yield N-phenyl imines. The participation of complex 5 as a nucleophile in these reactions and the previously reported reaction of 5 with PPh3 confirm the ambiphilic nature of (CO)5W=NPh. This is consistent with the electronic structure of the model compound (CO)5W=NMe, as obtained from extended Hückel calculations. The heteroatom-substituted nitrene complex (CO)5W=NNMe2 (7) is less electrophilic but still functions as a nucleophile in its reaction with PhCHO to give Me2NN=CHPh.

Original languageEnglish (US)
Pages (from-to)4871-4876
Number of pages6
JournalJournal of the American Chemical Society
Volume113
Issue number13
DOIs
StatePublished - Jun 1 1991

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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