《Identification and Reactivity of s-cis,s-cis-Dihydroxycarbene, a New [CH2O2] Intermediate》 was published in Journal of the American Chemical Society in 2020. These research results belong to Quanz, Henrik; Bernhardt, Bastian; Erb, Frederik R.; Bartlett, Marcus A.; Allen, Wesley D.; Schreiner, Peter R.. COA of Formula: C4H5ClO3 The article mentions the following:
We report the first preparation of the s-cis,s-cis conformer of dihydroxycarbene (1cc) by means of pyrolysis of oxalic acid, isolation of the lower-energy s-trans,s-trans (1tt) and s-cis,s-trans (1ct) product conformers at cryogenic temperatures in a N2 matrix, and subsequent narrow-band near-IR (NIR) laser excitation to give 1cc. Carbene 1cc converts quickly to 1ct via quantum-mech. tunneling with an effective half-life of 22 min at 3 K. The potential energy surface features around 1 were pinpointed by convergent focal point anal. targeting the AE-CCSDT(Q)/CBS level of electronic structure theory. Computations of the tunneling kinetics confirm the time scale of the 1cc → 1ct rotamerization and suggest that direct 1cc → H2 + CO2 decomposition may also be a minor pathway. The intriguing latter possibility cannot be confirmed spectroscopically, but hints of it may be present in the measured kinetic profiles. The experimental part of the paper was very detailed, including the reaction process of Ethyl oxalyl monochloride(cas: 4755-77-5COA of Formula: C4H5ClO3)
Ethyl oxalyl monochloride(cas: 4755-77-5) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.COA of Formula: C4H5ClO3
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