The conversion of some carbohydrate diols into cyclic carbonates and thiocarbonates by means of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt)

1982 ◽  
Vol 35 (8) ◽  
pp. 1709 ◽  
Author(s):  
C Copeland ◽  
RV Stick
Keyword(s):  
Hydrogen Sulfide ◽  
Cyclic Carbonates ◽  
Sodium Hydrogen ◽  
Dimethylammonium Chloride ◽  
Vicinal Diols ◽  
Cis And Trans

Various carbohydrate cis and trans vicinal diols have been treated with N-dichloromethylene-N,N- dimethylammonium chloride (Viehe's salt), and the resulting cyclic salts quenched with water or sodium hydrogen sulfide to form, in the main, cyclic carbonates and thiocarbonates. These results are discussed in light of the 'orbital-assist' proposal by Deslongchamps.

The reaction of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt) with 1,2:5,6-di-O-isopropylidene-a-D-glucose

1982 ◽  
Vol 35 (11) ◽  
pp. 2269 ◽  
Author(s):  
C Copeland ◽  
RV Stick
Keyword(s):  
Hydrogen Sulfide ◽  
Ammonium Chloride ◽  
Iminium Salts ◽  
Dimethyl Ammonium Chloride ◽  
Sodium Hydrogen ◽  
Dimethylammonium Chloride ◽  
Dimethyl Ammonium

The treatment of 1,2:5,6-di-O-isopropylidene-α-D-glucose with N-dichloromethylene-N,N-dimethyl ammonium chloride (Viehe's salt) (2: 1 or 1 : 1) gives two iminium salts. These are readily hydrolysed to a carbonate and a carbamate. Treatment with sodium hydrogen sulfide gave some thiocarbonate and thiocarbamate. One of the iminium salts underwent a base-induced elimination to give 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-ribo-hex-3-enofuranose.

The reaction of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt) with thiophenols and phenols: a synthesis of unsymmetrical diaryl carbonates

1984 ◽  
Vol 37 (7) ◽  
pp. 1483 ◽  
Author(s):  
C Copeland ◽  
RV Stick
Keyword(s):  
Hydrogen Sulfide ◽  
Efficient Synthesis ◽  
Sodium Hydrogen ◽  
Dimethylammonium Chloride

The reaction of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt) with various thiophenols and phenols is reported. The resulting intermediate salts are generally transformed by water or sodium hydrogen sulfide to thiocarbonates and thiocarbamates. An efficient synthesis of unsymmetrical diaryl carbonates is discussed.

ChemInform Abstract: Reactions of 2-Substituted 3-Phenylpropenoyl Isothiocyanates with Sodium Hydrogen Sulfide.

ChemInform ◽  
1990 ◽  
Vol 21 (50) ◽  
Author(s):  
M. DZURILLA ◽  
P. KUTSCHY ◽  
D. KOSCIK ◽  
V. FICERI ◽  
R. KRAUS
Keyword(s):  
Hydrogen Sulfide ◽  
Sodium Hydrogen

Sodium Hydrogen Sulfide

2007 ◽  
pp. 128-131 ◽  
Author(s):  
Richard E. Eibeck ◽  
Ralph A. Zingaro ◽  
Raymond E. Mcglothlin
Keyword(s):  
Hydrogen Sulfide ◽  
Sodium Hydrogen

Iron-Catalyzed Synthesis of Five-Membered Cyclic Carbonates from Vicinal Diols: Urea as Sustainable Carbonylation Agent

2016 ◽  
Vol 2016 (22) ◽  
pp. 3721-3727 ◽  
Author(s):  
Miguel Peña-López ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Cyclic Carbonates ◽  
Vicinal Diols

9-Oxobenzomorphans. IV. 9-Oxo-5-[3″-(1″-hydroxypropyl)]- and 9-oxo-5-[3″-(1″-sulfidrylpropyl)]-6,7-benzomorphans as cyclic hemiketals and hemithioketals

1981 ◽  
Vol 59 (2) ◽  
pp. 321-325 ◽  
Author(s):  
Gerry Kavadias ◽  
Stephan Velkof
Keyword(s):  
Hydrogen Sulfide ◽  
Sodium Hydroxide ◽  
Sodium Hydrogen

The syntheses of 9-oxobenzomorphans 10 and 12 are described. Both products exist in the cyclic forms 11 and 13 respectively. Hydrobromide and oxalate salts of the 9-oxobenzomorphan 1 when crystallized from methanol form stable methylhemiketals 4 and 5. Bromination of 5 yielded benzomorphan 8 which on treatment with sodium hydroxide produced, via 10, the cyclic hemiketal 11. Reaction of 8 with sodium hydrogen sulfide afforded, via 12, the cyclic hemithioketals 13.

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