100946-72-3Relevant academic research and scientific papers
Flash Vacuum Thermolysis of 2,3-Dihydro-1,4-oxathiin: Synthesis, Photoelectronic Spectroscopy, and Dienophilic Reactivity of Thioxoethanal
Bourdon, Francois,Ripoll, Jean-Louis,Vallee, Yannick,Lacombe, Sylvie,Pfister-Guillouzo, Genevieve
, p. 2596 - 2600 (2007/10/02)
Thioxoethanal has been generated in the gas phase by vacuum thermolysis of 2,3-dihydro-1,4-oxathiin.Its characterization was performed by chemical trapping and photoelectron spectroscopy (PES).The PE HeI-HeII study led to the conclusion that thioxoethanal was obtained, with ethylene, as the only thermolysis product at 720 deg C.At higher temperatures, a cleavage into methanethial and carbon monoxide was observed.The results from the PE study, as well as MNDO calculations, indicate a very weak interaction between the formyl and thioformyl moieties of the molecule through the ? C-C bond.The HOMO sulfur lone pair is only slightly stabilized by the inductive effect of the carbonyl group.These conclusions account for the observed dienophilic reactivity of thioxoethanal.
Thioaldehyde Diels-Alder Reactions
Vedejs, E.,Eberlein, T. H.,Mazur, D. J.,McClure, C. K.,Perry, D. A.,et al.
, p. 1556 - 1562 (2007/10/02)
Thioaldehydes containing virtually any α-substitutent can be generated by photofragmentation of phenacyl sulfides.Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advan
