An Unprecedented [2+3] Cycloadditive Dimerization of a Transient Thiocarbonyl S-Ylide

4‐Chlorophenyl C‐(phenylsulfonyl)dithioformate reacts with diazo(trimethylsilyl)methane to form 2‐(4‐chlorophenylthio)‐2‐phenylsulfonyl‐4,5‐bis(trimethylsilyl)‐1,3‐dithiolan‐1‐ium (4‐chlorophenylthio)(phenylsulfonyl)methylide. It is assumed that this product is formed by [2+3] cycloadditive dimeriza...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-03, Vol.2003 (5), p.813-815
Main Authors: El-Sayed, Ibrahim, Grønbæk Hazell, Rita, Øgaard Madsen, Jørgen, Norrby, Per-Ola, Senning, Alexander
Format: Article
Language:English
Subjects:
Ab initio calculations
Cycloaddition
Sulfur
Ylides
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Summary:4‐Chlorophenyl C‐(phenylsulfonyl)dithioformate reacts with diazo(trimethylsilyl)methane to form 2‐(4‐chlorophenylthio)‐2‐phenylsulfonyl‐4,5‐bis(trimethylsilyl)‐1,3‐dithiolan‐1‐ium (4‐chlorophenylthio)(phenylsulfonyl)methylide. It is assumed that this product is formed by [2+3] cycloadditive dimerization of the transient (trimethylsilyl)methanethial S‐[(4‐chlorophenylthio)(phenylsulfonyl)methylide]. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200390123