- Interaction of acetonitrile with trifluoromethanesulfonic acid: Unexpected formation of a wide variety of structures
-
Interaction of acetonitrile with trifluoromethanesulfonic acid has been studied by multinuclear NMR and ESI-MS. It has been found that the interaction results in formation of a great variety of different cations and neutral compounds which is controlled by the ratio of CH3CN to TfOH. In the presence of an excess of the acid (molar ratio 1:8-14) diprotonated N-acetylacetamidine 1 is formed as the major product, which eventually transforms into protonated acetamidine 3 and acetic acid 4. At molar ratio of (1:1-2) diprotonated 2,4-dimethyl-6-methylidene-3H-1,3,5-triazine 12, tautomer of the diprotonated trimethyl-s-triazine 11, becomes the main product at an early stage of the reaction and diprotonated 1-(dimethyl-1,3,5-triazin-2-yl) prop-1-en-2-ol 15 at a later stage. In the case of a large excess of acetonitrile (4-20:1) trication 17 is formed as a result of the interaction between 11 and 12 along with some oligomers [(CH3CN) 3]n (n = 4-12). The Royal Society of Chemistry 2012.
- Salnikov, George E.,Genaev, Alexander M.,Vasiliev, Vladimir G.,Shubin, Vyacheslav G.
-
supporting information; experimental part
p. 2282 - 2288
(2012/04/10)
-
- Unusual aluminum chloride-assisted conversion of isopropenyl acetate into 3-acetyl- and 3,5-diacetyl-2,6-dimethyl-4H-pyran-4-ones
-
Reflux of isopropenyl acetate with an excess of AlCl3 in 1,2-dichloroethane affords 3,5-diacetyl-2,6-dimethyl-4H-pyran-4-one in 17% yield. The mild acidic cleavage of the latter (2% HCl, 20°C, 16 h) gives 3-acetyl-2,6-dimethyl-4H-pyran-4-one in 87% yield, whereas this reaction under more drastic conditions (17% HCl, reflux, 3 h) gives 2,6-dimethyl-4H-pyran-4-one in 61% yield.
- Novikov,Shestak,Denisenko
-
experimental part
p. 1600 - 1604
(2011/05/04)
-