Imidoylketene dimerization and rearrangement

George, L., Bernhardt, P. V., Netsch, K. P. and Wentrup, C. (2004) Imidoylketene dimerization and rearrangement. Organic & Biomolecular Chemistry, 2 23: 3518-3523. doi:10.1039/b412530d


Author George, L.
Bernhardt, P. V.
Netsch, K. P.
Wentrup, C.
Title Imidoylketene dimerization and rearrangement
Journal name Organic & Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
Publication date 2004
Sub-type Article (original research)
DOI 10.1039/b412530d
Open Access Status Not Open Access
Volume 2
Issue 23
Start page 3518
End page 3523
Total pages 6
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2004
Language eng
Abstract FVT of pyrroledione 10 affords the NH-imidoylketene 11, which is characterized by its matrix isolation IR spectrum ( 2117 cm 1). On warming above 170 K, 11 dimerizes to the oxazinone 13, the X-ray crystal structure of which is reported. Imidoylketene 11 also undergoes a (reversible) 1,3-phenyl shift to afford the detectable alpha-oxoketenimine 16 (2062 cm(-1)) which at FVT temperatures above 400degreesC, isomerizes to 2-cyano-2-phenylacetophenone 18 (optimally at 700degreesC). Moreover, imidoylketene 11 can cyclize to azetinone 19, detectable at FVT temperatures up to 570degreesC, which undergoes cycloreversion to diphenylacetylene 20 and isocyanic acid (HNCO) 21. Energy profiles calculated at the B3LYP/6-31G** level for the unsubstituted imidoylketene, the diphenylimidoylketene 11 and the N-tert-butylimidoylketene are also reported.
Keyword Chemistry, Organic
Ab-initio
Ketene-ketene
Meldrums Acid
Derivatives
1,3-migration
Formylketene
Reactivity
Molecules
Q-Index Code C1

 
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Created: Wed, 15 Aug 2007, 04:13:35 EST