The Claisen rearrangement of allyl vinyl ether in the gas phase and aqueous solution. Structures and energies predicted by high-level ab initio calculations

1995 ◽  
Vol 246 (6) ◽  
pp. 536-540 ◽  
Author(s):  
Mark M. Davidson ◽  
Ian H. Hillier ◽  
Mark A. Vincent
Keyword(s):  
Aqueous Solution ◽  
Ab Initio Calculations ◽  
Ab Initio ◽  
Gas Phase ◽  
Vinyl Ether ◽  
Claisen Rearrangement ◽  
Solution Structures ◽  
High Level

Halide–Nitrogen Gas-Phase Clusters: Anion Photoelectron Spectroscopy and High Level ab Initio Calculations

2015 ◽  
Vol 119 (37) ◽  
pp. 9722-9728 ◽  
Author(s):  
Kim M. L. Lapere ◽  
Marcus Kettner ◽  
Peter D. Watson ◽  
Allan J. McKinley ◽  
Duncan A. Wild
Keyword(s):  
Ab Initio Calculations ◽  
Ab Initio ◽  
Gas Phase ◽  
Photoelectron Spectroscopy ◽  
Nitrogen Gas ◽  
Gas Phase Clusters ◽  
Anion Photoelectron Spectroscopy ◽  
High Level

High-Level ab Initio Calculations on the Gas-Phase Reactions between C+(2P) and Formic Acid

1999 ◽  
Vol 103 (23) ◽  
pp. 4543-4552
Author(s):  
Ana I. González ◽  
Alberto Luna ◽  
Manuel Yáñez
Keyword(s):  
Formic Acid ◽  
Ab Initio Calculations ◽  
Ab Initio ◽  
Gas Phase ◽  
Gas Phase Reactions ◽  
High Level

Configurational Assignment and Conformational Study of Methylglyoxal Bisdimethylhydrazones Derived from the 2-Ethoxypropenal Precursor

2006 ◽  
Vol 59 (3) ◽  
pp. 211 ◽  
Author(s):  
Leonid B. Krivdin ◽  
Lyudmila I. Larina ◽  
Kirill A. Chernyshev ◽  
Natalia A. Keiko
Keyword(s):  
Ab Initio Calculations ◽  
Ab Initio ◽  
Experimental Measurements ◽  
Conformational Study ◽  
Lone Pairs ◽  
Configurational Assignment ◽  
Out Of Plane ◽  
High Level

A configurational assignment of the isomeric methylglyoxal bisdimethylhydrazones derived from the 2-ethoxypropenal precursor has been performed based on experimental measurements and high-level ab initio calculations of 1J(C,C) and 1J(C,H) couplings. The results reveal the marked stereochemical dependence upon the orientation of the lone pairs of both nitrogen atoms in different isomers. Methylglyoxal bisdimethylhydrazone is shown to exist in a mixture of the EE and ZE isomers (ca. 75:25), both of which adopt predominant s-trans conformations with minor (up to 8°) out-of-plane deviations.

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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