1, 1‐Ethenediol: The Long Elusive Enol of Acetic Acid. Issue 14 (12th February 2020)

• Record Type: Journal Article
• Authors: Mardyukov, Artur; Eckhardt, André K.; Schreiner, Peter R.
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 14(2020)
• Page Start: 5577
• Page End: 5580
• Publication Date: 2020-02-12
• Subjects: enol -- matrix isolation -- photochemistry -- prebiotic chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201915646
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We present the first spectroscopic identification of hitherto unknown 1, 1‐ethenediol, the enol tautomer of acetic acid. The title compound was generated in the gas phase through flash vacuum pyrolysis of malonic acid at 400 °C. The pyrolysis products were subsequently trapped in argon matrices at 10 K and characterized spectroscopically by means of IR and UV/Vis spectroscopy together with matching its spectral data with computations at the CCSD(T)/cc‐pCVTZ and B3LYP/6–311++G(2d, 2p) levels of theory. Upon photolysis at λ =254 nm, the enol rearranges to acetic acid and ketene. Abstract : Finally made : The hitherto unreported 1, 1‐ethenediol, the higher energy tautomer of acetic acid, was synthesized and spectroscopically characterized. It can be readily prepared through thermal decarboxylation of malonic acid, as has generally often been implied in the synthetically highly valuable reactions of 1, 3‐dicarboxylic acids.