Nuclear magnetic resonance of adducts of heterocyclic systems with nucleophiles. 27. 1,2,4,5-Tetrazine and its derivatives. 4. Carbon-13 nuclear magnetic resonance investigations of the anionic homoaromatic .sigma. adducts formed between liquid ammonia and 1,2,4,5-tetrazines

1981 ◽  
Vol 46 (19) ◽  
pp. 3805-3810 ◽  
Author(s):  
Anda Counotte-Potman ◽  
Henk C. Van der Plas ◽  
Beb Van Veldhuizen
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Liquid Ammonia ◽  
Nuclear Magnetic

Reductive cleavage with metal in liquid ammonia. III. Olefin formation from the reaction of sodium metal with methyl 4,6-O-ethylidene-3-O,S-dimethyl-2-thio-α-d-altropyranoside dissolved in 1,2-dimethoxyethane

1967 ◽  
Vol 45 (15) ◽  
pp. 1767-1775 ◽  
Author(s):  
U. G. Nayak ◽  
M. Sharma ◽  
R. K. Brown
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Liquid Ammonia ◽  
Reductive Cleavage ◽  
Metallic Sodium ◽  
Sodium Metal ◽  
Infrared Data ◽  
Nuclear Magnetic

Methyl 4,6-O-ethylidene-3-O,S-dimethyl-2-thio-α-d-altropyranoside, when heated in refluxing 1,2-dimethoxyethane with an equimolar quantity of metallic sodium, gave approximately a 75% yield of a mixture of the three olefins, methyl 2,3-didehydro-3-deoxy-4,6-O-ethylidene-S-methyl-2-thio-α-d-altropyranoside (XI), l,2-didehydro-l-deoxy-4,6-O-ethylidene-3-O,S-dimethyl-2-thio-d-ribo-hexopyranose (XII), and methyl 3,4-didehydro-3-deoxy-4,6-O-ethylidene-S-methyl-2-thio-α-d-erythro(or threo)-hexopyranoside (XIII) (tentative). Only compounds XI and XII could be separated and characterized. The structural assignments were based on a comparison with authentic samples and on nuclear magnetic resonance and infrared data, as well as on a comparison with the characteristics of analogous 4,6-O-benzylidene compounds previously reported (2).

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