Gas-phase Wittig rearrangement of carbanions derived from benzyl ethers

1986 ◽  
Vol 51 (26) ◽  
pp. 5078-5082 ◽  
Author(s):  
Peter C. H. Eichinger ◽  
John H. Bowie ◽  
Thomas Blumenthal
Keyword(s):  
Gas Phase ◽  
Wittig Rearrangement ◽  
Benzyl Ethers

ChemInform Abstract: Gas-Phase Wittig Rearrangement of Carbanions Derived from Benzyl Ethers.

ChemInform ◽  
1987 ◽  
Vol 18 (29) ◽  
Author(s):  
P. C. H. EICHINGER ◽  
J. H. BOWIE ◽  
T. BLUMENTHAL
Keyword(s):  
Gas Phase ◽  
Wittig Rearrangement ◽  
Benzyl 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.

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