The Smallest Vicinal Tricarbonyl Compound as a Monohydrate and Tetracarbonyl Compound as a Thiane Derivative – First Effective Synthesis, Characterization and Chemistry

✍ Scribed by Shyamaprosad Goswami; Annada C. Maity; Hoong-Kun Fun; Suchada Chantrapromma

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 850 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200801050

✦ Synopsis

Abstract

An effective synthesis of 2‐oxo‐1,3‐propanedial monohydrate or mesoxaldehyde (6a) and the first synthesis of 2,3‐dioxo‐1,4‐butanedial (18) as a thiane derivative are reported. These first members of the smallest vicinal tri‐ and tetracarbonyl compounds are stabilized by conversion to thiane derivatives 8, 9, 10, 11, 12, 15 and 19, which can be isolated as long‐lived compounds at room temperature. The structures of these novel thianes 8, 10, 12 and 15 were confirmed by their X‐ray crystal structures. The synthesis of a series of protected as well as free heterocyclic aldehydes (pterins and quinoxalines) by the use of the appropriate tricarbonyl compounds is also reported. Additionally, a one‐step synthetic strategy to prepare a series of different biheterocycles with the smallest vicinal tetracarbonyl compound is demonstrated.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)