Gas-phase carbanion rearrangements. Does the Wittig rearrangement occur for deprotonated vinyl ethers?

1990 ◽  
pp. 1763 ◽  
Author(s):  
Peter C. H. Eichinger ◽  
John H. Bowie
Keyword(s):  
Gas Phase ◽  
Vinyl Ethers ◽  
Wittig Rearrangement

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.

Experimental and theoretical studies of the gas-phase protonation of vinyl ethers, vinyl sulfides, and vinyl selenides

1989 ◽  
Vol 111 (14) ◽  
pp. 5028-5036 ◽  
Author(s):  
K. Osapay ◽  
J. Delhalle ◽  
K. M. Nsunda ◽  
E. Rolli ◽  
R. Houriet ◽  
...  
Keyword(s):  
Gas Phase ◽  
Theoretical Studies ◽  
Vinyl Ethers ◽  
Vinyl Sulfides ◽  
Experimental And Theoretical Studies

Stereochemistry and Mechanism of Vinyl-migrating [1,2]-Wittig Rearrangement ofα-Lithioalkyl Vinyl Ethers

2000 ◽  
Vol 29 (4) ◽  
pp. 418-419 ◽  
Author(s):  
Katsuhiko Tomooka ◽  
Tadashi Inoue ◽  
Takeshi Nakai
Keyword(s):  
Vinyl Ethers ◽  
Wittig Rearrangement

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

Synthetic Applications of Intramolecular Insertion in Arylcarbenes. III. Generation and Rearrangement of Aryloxycarbenes by Intramolecular Abstraction of Hydrogen

1979 ◽  
Vol 32 (1) ◽  
pp. 111 ◽  
Author(s):  
WD Crow ◽  
H McNab
Keyword(s):  
Gas Phase ◽  
Hydrogen Abstraction ◽  
Low Pressure ◽  
Insertion Reactions ◽  
Vinyl Ethers ◽  
Deuterium Labelling ◽  
Hydride Shift

o-Alkoxy- and o-alkylthio-phenylcarbenes, generated by low-pressure pyrolysis in the gas phase, show abstraction of 2H across space to generate the corresponding o-tolyl vinyl ethers or sulfides. In the case of o-ethoxyphenylcarbene, deuterium labelling shows that this is a case of vicinal abstraction, not geminal abstraction followed by 1,2-hydride shift. o-Methoxyphenylcarbene, however, is similarly shown to undergo geminal hydrogen abstraction leading to o-tolyloxycarbene, which undergoes a 1,2-aryl shift to give o-tolualdehyde. Independent generation of aryloxycarbenes has been achieved by pyrolysis of 5-aryloxy-2,2-dimethyl-l,3-dioxan- 4,6-diones. The product carbenes show the expected rearrangement as well as normal insertion reactions.

Kinetic Study of Gas-Phase Reactions of OH and NO3 Radicals and O3 with iso-Butyl and tert-Butyl Vinyl Ethers

2012 ◽  
Vol 116 (35) ◽  
pp. 8885-8892 ◽  
Author(s):  
Shouming Zhou ◽  
Ian Barnes ◽  
Tong Zhu ◽  
Thorsten Benter
Keyword(s):  
Kinetic Study ◽  
Gas Phase ◽  
Gas Phase Reactions ◽  
Vinyl Ethers ◽  
Tert Butyl

Kinetic and Mechanistic Study of the Gas-Phase Reactions of a Series of Vinyl Ethers with the Nitrate Radical

2006 ◽  
Vol 110 (38) ◽  
pp. 11074-11081 ◽  
Author(s):  
Michaël Scarfogliero ◽  
Bénédicte Picquet-Varrault ◽  
Julien Salce ◽  
Régine Durand-Jolibois ◽  
Jean-François Doussin
Keyword(s):  
Gas Phase ◽  
Mechanistic Study ◽  
Nitrate Radical ◽  
Gas Phase Reactions ◽  
Vinyl Ethers
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