102437-87-6Relevant academic research and scientific papers
Studies on the Preparation of Dihydro-1,4-oxathiines. Computer-Assisted Evaluation of the Results of Retrosynthetic Analysis Verified by Synthetic Experiments and By-Product Analyses. Synthetic Pathways Involving α-Sulfenylated Ketones and 1,3-Oxathiolanes of α-Halo and α-Hydroxy K...
Nevalainen, Vesa,Pohjala, Esko,Maelkoenen, Pentti,Hukkanen, Heikki
, p. 591 - 602 (2007/10/02)
The preparation of 2- and 2,3-substituted 5,6-dihydro-1,4-oxathiines has been studied by computer simulation and by experiment.Three major synthetic pathways, involving 2-(1-hydroxyalkyl)-1,3-oxathiolanes, 2-(1-haloalkyl)-1,3-oxathiolanes, 2-hydroxyethylthiomethyl ketones, methanesulfonates of 2-hydroxyethylthiomethyl ketones and 2-choroethylthiomethyl ketones as intermediates, were evaluated, by running the program CAMEO, and by experiment.The results of the two approaches were compared and the major by-products of the reactions were identified by GLC/MS.
Studies on the Formation of Dihydro-1,4-oxathiines by Halogenation of 1,3-Oxathiolanes.
Nevalainen, Vesa,Pohjala, Esko
, p. 1401 - 1421 (2007/10/02)
Formation of 5,6-dihydro-1,4-oxathiines (1a-g) by halogenation of 1,3-oxathiolanes (4a-g) was investigated.Moderate yields of (1) were obtained in systems in which the newly formed double bond of the heterocyclic ring was stabilised by conjugation.In addition to the dihydro-1,4-oxathiines (1a-g), their halogenated derivatives and some fused and spiro 1,4-oxathianes were produced as by-products.By-products of reactions were analysed by gas chromatography and mass-spectrometry.
Synthesis of Dihydro-1,4-oxathiins by Action of Chlorine on 1,3-Oxathiolanes
Lee, Wha Suk,Park, Oee Sook,Choi, Joong Kwon,Nam, Kee Dal
, p. 5374 - 5377 (2007/10/02)
A new convenient synthesis of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid derivatives 1 has been achieved by using the action of chlorine on 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide (4a) and 2-methyl-1,3-oxathiolane-2-acetic acid methyl ester (4b).From the initially formed chlorosulfonium salts 16 unobserved transient sulfenyl chlorides 5 were generated, followed by cyclization to probable oxonium ion 18 to produce dihydrooxathiins 1.In the chlorinolysis reactions of 4a and 4b minor byproducts were formed: respectively 2,3-dichloro-2-methyl-1,4-oxathiin-3-carboxanilide 12a and its methyl ester analogue 12b.While 12b was stable, 12a was unstable, transforming to the corresponding 2-chloromethyl compound 13.The mechanism of formation of 13 as well as relative stability of dichlorides 12a, 12b, and related compounds is also discussed.
