Nucleophilic substitution at bivalent sulphur. Part IV. A mechanistic study of the base-catalysed hydrolysis of derivatives of 2-nitro-4-trifluoromethylbenzenesulphenic acid using 19F nuclear magnetic resonance spectroscopy

1974 ◽  
pp. 436 ◽  
Author(s):  
Donald R. Hogg ◽  
Joseph Stewart
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
Nucleophilic Substitution ◽  
Nuclear Magnetic Resonance Spectroscopy ◽  
Mechanistic Study ◽  
Resonance Spectroscopy ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Nuclear Magnetic

Nucleophilic substitution of vinylic halogens in 3-halomethacrylonitriles. Some observations on olefin stabilities

1970 ◽  
Vol 48 (13) ◽  
pp. 2104-2109 ◽  
Author(s):  
D. V. Gardner ◽  
D. E. McGreer
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
Nucleophilic Substitution ◽  
Nuclear Magnetic Resonance Spectroscopy ◽  
Resonance Spectroscopy ◽  
Nuclear Magnetic

3-Chloro- and 3-bromomethacrylonitrile (E- and Z-) have been shown to undergo nucleophilic substitution at C-3 with > 95% retention of configuration. The configuration of each product has been established by the use of nuclear magnetic resonance spectroscopy. The thermodynamic position of equilibrium for each pair of E–Z isomers has been determined and the factors which affect this equilibrium are discussed. Some form of cis interactions, non-steric in origin, dominates in determining the equilibrium positions.

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