Stereochemistry of nucleophilic addition reactions. 2. Kinetically controlled reaction of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-.beta.-D-erythro-hex-2-enopyranoside with hydrogen cyanide. Important role of electrostatic interaction

1977 ◽  
Vol 42 (10) ◽  
pp. 1746-1750 ◽  
Author(s):  
Tohru Sakakibara ◽  
Rokuro Sudoh
Keyword(s):  
Electrostatic Interaction ◽  
Hydrogen Cyanide ◽  
Nucleophilic Addition ◽  
Addition Reactions ◽  
Kinetically Controlled

ULTRAVIOLET IRRADIATION OF PYRIMIDINE DERIVATIVES: III. INFLUENCE OF HYDROGEN CYANIDE ON THE PHOTOLYSIS

1959 ◽  
Vol 37 (8) ◽  
pp. 1281-1287 ◽  
Author(s):  
A. M. Moore
Keyword(s):  
Nucleic Acids ◽  
Ultraviolet Irradiation ◽  
Hydrogen Cyanide ◽  
Nucleophilic Addition ◽  
Simple Calculation ◽  
Pyrimidine Derivative ◽  
Addition Reactions ◽  
Pyrimidine Derivatives ◽  
General Significance

The presence of HCN in concentrations up to 0.05 M in aqueous, buffered solutions of uracil, uridine, and 1,3-dimethyluracil has been shown to divert the normal course of the photochemical hydration reactions of these compounds as a result of photochemically induced combination between HCN and the pyrimidine derivative. A simple calculation indicates that HCN is more efficient than water in reacting with activated uracil molecules by a factor of about 103. The possible general significance of such nucleophilic addition reactions in the photochemistry of nucleic acids is discussed.

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