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 Citations (Scopus)

Abstract

(CO)5 W=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
StatePublished - 1991
Externally publishedYes

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Carbonyl compounds
Nucleophiles
Imines
Ketones
Aldehydes
Electronic structure
Substrates
compound W
phenylnitrene

ASJC Scopus subject areas

  • Chemistry(all)

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Evidence for ambiphilic behavior in (CO)5W=NPh. Conversion of carbonyl compounds to N-phenyl imines via metathesis. / Arndtsen, Bruce A.; Sleiman, Hanadi F.; Chang, Andrew K.; McElwee-White, Lisa.

In: Journal of the American Chemical Society, Vol. 113, No. 13, 1991, p. 4871-4876.

Research output: Contribution to journalArticle

Arndtsen, Bruce A. ; Sleiman, Hanadi F. ; Chang, Andrew K. ; McElwee-White, Lisa. / Evidence for ambiphilic behavior in (CO)5W=NPh. Conversion of carbonyl compounds to N-phenyl imines via metathesis. In: Journal of the American Chemical Society. 1991 ; Vol. 113, No. 13. pp. 4871-4876.
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