Dipivaloylketene and Its Unusual Dimerization to a Permanently Stable α-Oxoketene

Kappe C.O., Evans R.A., Kennard C.H.L. and Wentrup C. (1991) Dipivaloylketene and Its Unusual Dimerization to a Permanently Stable α-Oxoketene. Journal of the American Chemical Society, 113 11: 4234-4237. doi:10.1021/ja00011a027


Author Kappe C.O.
Evans R.A.
Kennard C.H.L.
Wentrup C.
Title Dipivaloylketene and Its Unusual Dimerization to a Permanently Stable α-Oxoketene
Journal name Journal of the American Chemical Society   Check publisher's open access policy
ISSN 0002-7863
Publication date 1991-01-01
Year available 1991
Sub-type Article (original research)
DOI 10.1021/ja00011a027
Open Access Status Not yet assessed
Volume 113
Issue 11
Start page 4234
End page 4237
Total pages 4
Place of publication WASHINGTON
Publisher AMER CHEMICAL SOC
Language eng
Subject 1600 Chemistry
Abstract Dipivaloylketene (8) is obtained by flash vacuum pyrolysis of 5-tert-butyl-4-pivaloyl-2,3-dihydrofuran-2,3-dione (7) at temperatures between 250 and 500-degrees-C. It is stable in solution below 0-degrees-C and dimerizes at room temperature to 10, which involves an unusual [2+4] cycloaddition reaction between one alpha-oxoketene unit and the carbonyl double bond of a second molecule, thus preserving the ketene functionality. The structure of the highly hindered ketene 10 was proved by X-ray crystallography. This compound is stable for months in the open air at high humidity.
Keyword Conjugated Ketenes
Rearrangement
Vinylketene
Q-Index Code C1
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 51 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 50 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Created: Tue, 13 Sep 2016, 13:55:53 EST by System User