ISSN:
0009-2940
Keywords:
Furan-2,3-diones
;
Pyrrol-2,3-diones
;
Cumulenes, S-hetero
;
Cycloaddition reactions
;
17O Labeling
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reactions of Cyclic Oxalyl Compounds, 35[1]. - Mechanistic Investigation Aided by Isotopic Labeling, 11[2]. - On the Reaction of 4-Benzoyl-5-phenylfuran-2,3-dione with S-Heterocumulenes - Preparative and Mechanistic Aspects[3]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 [4 + 2] 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.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260916
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