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 language | English (US) |
|---|---|
| Pages (from-to) | 4871-4876 |
| Number of pages | 6 |
| Journal | Journal of the American Chemical Society |
| Volume | 113 |
| Issue number | 13 |
| State | Published - 1991 |
| Externally published | Yes |
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ASJC Scopus subject areas
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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 journal › Article
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TY - JOUR
T1 - Evidence for ambiphilic behavior in (CO)5W=NPh. Conversion of carbonyl compounds to N-phenyl imines via metathesis
AU - Arndtsen, Bruce A.
AU - Sleiman, Hanadi F.
AU - Chang, Andrew K.
AU - McElwee-White, Lisa
PY - 1991
Y1 - 1991
N2 - (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.
AB - (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.
UR - http://www.scopus.com/inward/record.url?scp=0001278647&partnerID=8YFLogxK
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M3 - Article
AN - SCOPUS:0001278647
VL - 113
SP - 4871
EP - 4876
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 13
ER -