Application In Synthesis of Benzophenone. In 2021.0 MOLECULES published article about THIOCARBONYL S-METHANIDES; EFFICIENT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; FERROCENYL THIOKETONES; ALPHA-NITROSOALKENES; HETARYL; ARYL; CHEMISTRY; 1,2-DIAZA-1,3-DIENES; THIOCHALCONES in [Mloston, Grzegorz; Urbaniak, Katarzyna; Sobiecka, Malwina] Univ Lodz, Fac Chem, Dept Organ & Appl Chem, 12 Tamka St, PL-91403 Lodz, Poland; [Heimgartner, Heinz] Univ Zurich, Dept Chem, Winterthurerstr 190, CH-8057 Zurich, Switzerland; [Wuerthwein, Ernst-Ulrich] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany; [Wuerthwein, Ernst-Ulrich] Westfalische Wilhelms Univ Munster, Ctr Multiscale Theory & Computat CMTC, Corrensstr 40, D-48149 Munster, Germany; [Zimmer, Reinhold; Lentz, Dieter; Reissig, Hans-Ulrich] Free Univ Berlin, Inst Chem & Biochem, Takustr 3, D-14195 Berlin, Germany in 2021.0, Cited 67.0. The Name is Benzophenone. Through research, I have a further understanding and discovery of 119-61-9.
The hetero-Diels-Alder reactions of in situ-generated azoalkenes with thioketones were shown to offer a straightforward method for an efficient and regioselective synthesis of scarcely known N-substituted 1,3,4-thiadiazine derivatives. The scope of the method was fairly broad, allowing the use of a series of aryl-, ferrocenyl-, and alkyl-substituted thioketones. However, in the case of N-tosyl-substituted cycloadducts derived from 1-thioxo-2,2,4,4-tetramethylcyclobutan-3-one and the structurally analogous 1,3-dithione, a more complicated pathway was observed. By elimination of toluene sulfinic acid, the initially formed cycloadducts afforded 2H-1,3,4-thiadiazines as final products. Advanced DFT calculations revealed that the observed high regioselectivity was due to kinetic reaction control and that the (4 + 2)-cycloadditions of sterically less unhindered thiones occurred via highly unsymmetric transition states with shorter C..S-distances (2.27-2.58 angstrom) and longer N..C-distances (3.02-3.57 angstrom). In the extreme case of the sterically very hindered 2,2,4,4-tetramethylcyclobutan-1,3-dione-derived thioketones, a zwitterionic intermediate with a fully formed C-S bond was detected, which underwent ring closure to the 1,3,4-thiadiazine derivative in a second step. For the hypothetical formation of the regioisomeric 1,2,3-thiadiazine derivatives, the DFT calculations proposed more symmetric transition states with considerably higher energies.
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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem