Reactivity of carbenes and ketenes in low-temperature matrices. Carbene CO trapping, Wolff rearrangement, and ketene-pyridine ylide (zwitterion) observation

Visser P., Zuhse R., Wong M.W. and Wentrup C. (1996) Reactivity of carbenes and ketenes in low-temperature matrices. Carbene CO trapping, Wolff rearrangement, and ketene-pyridine ylide (zwitterion) observation. Journal of the American Chemical Society, 118 50: 12598-12602. doi:10.1021/ja962672o


Author Visser P.
Zuhse R.
Wong M.W.
Wentrup C.
Title Reactivity of carbenes and ketenes in low-temperature matrices. Carbene CO trapping, Wolff rearrangement, and ketene-pyridine ylide (zwitterion) observation
Journal name Journal of the American Chemical Society   Check publisher's open access policy
ISSN 0002-7863
Publication date 1996-12-18
Year available 1996
Sub-type Article (original research)
DOI 10.1021/ja962672o
Open Access Status Not yet assessed
Volume 118
Issue 50
Start page 12598
End page 12602
Total pages 5
Place of publication WASHINGTON
Publisher AMER CHEMICAL SOC
Language eng
Subject 1600 Chemistry
Abstract Dicarbalkoxyketenes 8a and 8b are obtained by photolysis of diazo esters 7 in cryogenic matrices or by FVT of 7 followed by matrix isolation. The photochemical Wolff rearrangement of diazomalonates 1 in Ar matrix at temperatures as low as 6.5 K produces alkoxy(alkoxycarbonyl)ketenes 3, also obtained by FVT of 1. Photolysis of 1 in CO matrix at greater than or equal to 6.5 K produces the dicarbalkoxyketenes 8. Ketenes 3, 8, and 12 react with pyridine above 40 K to produce ketene-pyridine ylides (zwitterions) 9, 10, and 13, respectively.
Keyword Laser Flash-Photolysis
Methyl Diazomalonate
Mechanism
Diazonaphthoquinones
Ketocarbenes
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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