Investigation of quantitative structure–reactivity relationships in the aliphatic Claisen rearrangement of bis-vinyl ethers reveals a dipolar, dissociative mechanism

2014 ◽  
Vol 12 (8) ◽  
pp. 1292-1308 ◽  
Author(s):  
Natasha F. O'Rourke ◽  
Jeremy E. Wulff
Keyword(s):  
Vinyl Ether ◽  
Claisen Rearrangement ◽  
Substituent Effects ◽  
Quantitative Structure ◽  
Vinyl Ethers ◽  
Dissociative Mechanism ◽  
Mechanism Of Reaction ◽  
Kinetic Investigations

Kinetic investigations of substituent effects in the Claisen rearrangement of bis-vinyl ether substrates suggest a dissociative mechanism of reaction.

ChemInform Abstract: Organo-Aluminum-Promoted Claisen Rearrangement of Bisallyl Vinyl Ethers.

ChemInform ◽  
1989 ◽  
Vol 20 (38) ◽  
Author(s):  
K. MARUOKA ◽  
H. BANNO ◽  
K. NONOSHITA ◽  
H. YAMAMOTO
Keyword(s):  
Claisen Rearrangement ◽  
Vinyl Ethers

Carbanion Rearrangements in the Gas Phase: The Unusual Claisen Rearrangement of Deprotonated Allyl Vinyl Ether

1990 ◽  
Vol 43 (9) ◽  
pp. 1479 ◽  
Author(s):  
PCH Eichinger ◽  
JH Bowie
Keyword(s):  
Gas Phase ◽  
Vinyl Ether ◽  
Condensed Phase ◽  
Claisen Rearrangement ◽  
Negative Ions ◽  
Marked Contrast ◽  
Wittig Rearrangement ◽  
Major Reaction

Allyl vinyl ether is reported to undergo a facile Wittig rearrangement to yield penta-1,4-dien-3-ol under base- catalysed conditions in the condensed phase. In marked contrast, the Wittig rearrangement is not a major reaction in the gas phase. Instead, initial rearrangement occurs by a Claisen process and subsequent fragmentations involve some of the most complex interconversions yet proposed for negative ions.

Stereochemical aspects of the Claisen rearrangement of allyl vinyl ethers

1975 ◽  
Vol 40 (1) ◽  
pp. 86-92 ◽  
Author(s):  
Herbert O. House ◽  
Jacek Lubinkowski ◽  
James J. Good
Keyword(s):  
Claisen Rearrangement ◽  
Vinyl Ethers ◽  
Allyl Vinyl Ethers
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