1772-43-6Relevant articles and documents
An alternative approach to differentially substituted 2-oxazoline chalcogen derivatives
De Mello, Murilo B.M.,Clososki, Giuliano C.,Piovan, Leandro,De Oliveira, Alfredo R.M.
, p. 11 - 16 (2015/07/02)
In this study we present an alternative method to obtain several substituted mono or bis-2-oxazolines containing a chalcogen atom as a tether element. Alkylation of 2-tosyloximethylene-2-oxazoline with an appropriate sodium, lithium or potassium alkoxide yielded the corresponding ether. Introduction of sulfur or selenium was easily accomplished using the corresponding sodium salts. The 77Se NMR for alkyl or aryl 2-methylene-2-oxazoline selenides shows good correlation with the electronegativity pattern of substituents. Most products containing oxazolinyl-chalcogen were stable under the usual experimental conditions. However, the tellurium derivatives showed unusual sensitivity to light and oxygen, decomposing through a very complex mechanistic pathway. As a result of this oxidative process, 4,4-dimethyl-2-oxazoline-2-carbaldehyde could be isolated and fully characterized for the first time, in 17% yield.
Generation of cyclic ketene-N,X-acetals (X = O, S) from 2-alkyl-1,3-oxazolines and 2-alkyl-1,3-thiazolines. Reactions with acid chlorides, 1,3-diacid chlorides and N-(chlorocarbonyl) isocyanate
Zhou, Aihua,Pittman Jr., Charles U.
, p. 37 - 48 (2007/10/03)
2-Alkyl-1,3-oxazolines, 2-alkyl-1,3-thiazolines, and the corresponding cyclic ketene-N,X-acetals (X = O, S) derived from them were reacted with monoacid chlorides, diacid chlorides, triacid chlorides. A series of these carbon-carbon bond-forming reactions and cyclizations to both substituted 2,3-dihydrooxazolo[3,2-a]pyridine-5,7-diones and 2,3-dihydrothiazolo[3,2-a] pyridine-5,7-diones proceeded under mild reaction conditions. Cyclic ketene-N,X-acetal intermediates play important roles in all these reactions. Related cyclizations with N-(chlorocarbonyl) isocyanate formed substituted 2,3-dihydrooxazolo[3,2-c]pyrimidine-5,7-diones and 2,3-dihydrothiazolo[3,2-c] pyrimidine-5,7-diones. Georg Thieme Verlag Stuttgart.
Decomposition of alkene adducts of thianthrene cation radical in nitrile solvents. Formation of alkyl-2-oxazolines and a new class of four-component products: 5-[(1-alkoxyalkylidene) ammonio]alkylthianthrenium diperchlorates
Shine, Henry J.,Zhao, Bing-Jun,Marx, John N.,Ould-Ely, Teyeb,Whitmire, Kenton H.
, p. 9255 - 9261 (2007/10/03)
The monoadducts (4a-d) of thianthrene cation radical perchlorate (1a) and isobutene, 2-methyl-butene, 2-methyl-2-butene, and 2-methylpentene decompose spontaneously in acetonitrile (MeCN) solution, with the formation of thianthrene (Th). Decomposition of 4a (1,2-(5,10-thianthreniumdiyl)-2-methylpropane diperchlorate) and 4a', the corresponding dihexafluorophosphate, was studied in depth and extensively with 1H and 13C NMR spectroscopy. Decomposition of 4a was found to involve the solvent itself as well as water in the solvent, remaining from incomplete drying, and gave, apart from Th, successively, the perchlorate salts of 2,4,4-trimethyl-2-oxazoline (6) and 2-amino-2-methylpropyl acetate (7). These salts, 6-HCIO4 and 7-HCIO4, respectively, were prepared and used in understanding the reactions of 4a as well as the relationships among 6, 7, and 2-(acetylamino)-2-methyl propanol (8) in acidified MeCN solution. Decompositions of 4a-d in MeCN and other nitriles (RCN) containing an added alcohol (ROH) led to new products, 5-[(1-alkoxyalkylidene)ammonio]alkylthianthrenium diperchlorates (5a-u). These compounds were identified with 1H and 13C NMR spectroscopy and, in part, with X-ray crystallography and elemental analysis. The mechanisms of formation of 5-7 are discussed.
