On the chemistry of stable alpha-oxoketenes

Kollenz, Gert, Heilmayer, Werner, Kappe, C. Oliver, Wallfisch, Bianca and Wentrup, Curl (2001) On the chemistry of stable alpha-oxoketenes. Croatica Chemica Acta, 74 4: 815-823.

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Author Kollenz, Gert
Heilmayer, Werner
Kappe, C. Oliver
Wallfisch, Bianca
Wentrup, Curl
Title On the chemistry of stable alpha-oxoketenes
Formatted title
On the chemistry of stable α-oxoketenes
Journal name Croatica Chemica Acta   Check publisher's open access policy
ISSN 0011-1643
1334-417X
Publication date 2001-11
Year available 2001
Sub-type Critical review of research, literature review, critical commentary
Open Access Status File (Publisher version)
Volume 74
Issue 4
Start page 815
End page 823
Total pages 9
Place of publication Zagreb, Croatia
Publisher Hrvatsko Kemijsko Drustvo
Language eng
Subject C1
250303 Physical Organic Chemistry
780103 Chemical sciences
Formatted abstract
This short review describes the preparation and chemistry of sterically stabilized alpha -oxoketenes, which can be isolated and handled as true neat compounds. Their reactions with dienophiles afford [4+2] - as well as [2+2] cycloadducts depending on their ability to adopt that conformation suitable for each type of cycloaddition reactions. Addition of nucleophiles leads either to dipivaloylacetic acid derivatives as expected products or to the rare molecular skeleton of mono- or bifunctionalized bridged bisdioxines, which exhibit axial chirality. The bifunctionalized derivatives may serve as novel spacer units in several macrocyclic systems.
Keyword α-Oxoketenes
Preparation and chemistry
Cycloaddition reactions
Addition of nucleophiles
Bridged bisdioxines
Macrocycles
Chemistry, Multidisciplinary
alpha-Oxoketenes
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Critical review of research, literature review, critical commentary
Collection: School of Chemistry and Molecular Biosciences
 
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Created: Tue, 14 Aug 2007, 15:30:35 EST