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Synlett 1991; 1991(4): 287-288
DOI: 10.1055/s-1991-21980
DOI: 10.1055/s-1991-21980
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Generaton of Thiocarbonyl Ylides from the Rhodium(II) -Catalyzed Cyclization of Diazothiocarbonyl Compounds
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Publikationsdatum:
07. März 2002 (online)
![](https://www.thieme-connect.de/media/synlett/199104/lookinside/thumbnails/10.1055-s-1991-21980-1.jpg)
The rhodium(II)-catalyzed reaction of an α-diazoβ-oxo esters containing a thiocarbonyl group (ethyl 2-diazo-5-(N-methyl-N-phenylthiocarbamoyl)-3-oxopentanoate produced a cyclic thiocarbonyl ylide which extruded sulfur via a transient episulfide intermediate to give ethyl 2-(N-methyl-N-phenylamino)-5-oxo-2-cyclopentene-1-carboxylate. The mesoionic anhydro-4-hydroxythiazolium hydroxide system derived from cyclization of a diazothioamide [methyl 2-diazo-3-oxo-3-(2-thioxo-1-pyrrolidinyl)-propanoate] underwent a 1,3-dipolar cycloaddition in the presence of N-phenylmaleimide to give methyl 4,9a-epithio-2-phenyl-1,3,5-trioxoperhydropyrrole[3,4-g]-indolizine-4-carboxylate.