Electrochemical studies of tungsten hexafluoride and related compounds in anhydrous hydrogen fluoride

1975 ◽  
Vol 14 (10) ◽  
pp. 2408-2412 ◽  
Author(s):  
A. M. Bond ◽  
I. Irvine ◽  
T. A. O'Donnell
Keyword(s):  
Hydrogen Fluoride ◽  
Electrochemical Studies ◽  
Tungsten Hexafluoride ◽  
Anhydrous Hydrogen Fluoride ◽  
Related Compounds

Nucleic acid related compounds. 34. Non-aqueous diazotization with tert-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides

1981 ◽  
Vol 59 (17) ◽  
pp. 2608-2611 ◽  
Author(s):  
Morris J. Robins ◽  
Bogdan Uznański
Keyword(s):  
Nucleic Acid ◽  
Hydrogen Fluoride ◽  
Antimony Trichloride ◽  
Anhydrous Ammonia ◽  
Pyridine Hydrochloride ◽  
Tert Butyl ◽  
Anhydrous Hydrogen Fluoride ◽  
Related Compounds

Treatment of 2,6-diamino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (1c) with tert-butyl nitrite (TBN) in 60% anhydrous hydrogen fluoride/pyridine at −20 °C gave 2-fluoroadenosine triacetate (2) in 48% yield. Analogous treatment of the acetylated 2-amino-6-fluoropurine nucleoside (1a) gave the 2,6-difluoro compound (3a) in 63% yield. Anhydrous ammonia in 1,2-dimethoxy-ethane converted 3a → 2 without ammonolysis of the acetate groups. The overall conversion of 1a → 3a → 2 without isolation of 3a proceeded in 80% yield. Similar diazotization of the 2-amino-6-chloro nucleoside (1b) in HF/pyridine gave the 2-fluoro-6-chloro analogue (3b) in 89% yield. Treatment of 1b with TBN and pyridine hydrochloride in dichloromethane (77%) or TBN and antimony trichloride in 1,2-dichloroethane (84%) gave the 2,6-dichloropurine nucleoside (4b). The latter conditions converted 1a to the 2-chloro-6-fluoro product (4a) in 77% yield. Conversions of 1a and 1b to the 2-bromo-6-fluoro (5a, 67%) and 2-bromo-6-chloro (5b, 78%) analogues were effected using TBN and antimony tribromide in dibromomethane.

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