154840-92-3Relevant academic research and scientific papers
Reactions of Cyclic Oxalyl Compounds, 35. - Mechanistic Investigation Aided by Isotopic Labeling, 11. - On the Reaction of 4-Benzoyl-5-phenylfuran-2,3-dione with S-Heterocumulenes - Preparative and Mechanistic Aspects
Heilmayer, Werner,Kappe, Oliver C.,Sterk, Heinz,Kollenz, Gert,Peters, Karl,et al.
, p. 2061 - 2068 (2007/10/02)
The furan-2,3-dione 1 combines with N-sulfinylamines or sulfur diimides to afford the pyrrole-2,3-diones 2, while with N-tosylsulfinylamine the (α-iminobenzyl)furandione 3 is obtained. (α-Iminobenzyl)pyrrolediones 4 are formed in the reaction of 2c with N-tosylsulfinylamine or from 3 with N-tosylsulfur diimides.Diisopropylcarbodiimide and the pyrroledione 2c or the (iminobenzyl)furandione 3a undergo cycloaddition reactions accompanied by novel and surprising rearrangements to furnish the bicyclic compounds 5 and 6, respectively.The molecular skeleton of 6 was confirmed by an X-ray diffraction analysis.With the aid of 17O-labeling experiments and 17O-NMR spectroscopy mechanistic pathways including novel rearrangements were made evident. - Key Words: Furan-2,3-diones/ Pyrrol-2,3-diones/ Cumulenes, S-hetero/ Cycloaddition reactions/ 17O Labeling
