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An Unprecedented [2+3] Cycloadditive Dimerization of a Transient Thiocarbonyl S ‐Ylide
Author(s) -
ElSayed Ibrahim,
Grønbæk Hazell Rita,
Øgaard Madsen Jørgen,
Norrby PerOla,
Senning Alexander
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390123
Subject(s) - trimethylsilyl , ylide , chemistry , diazo , transient (computer programming) , medicinal chemistry , methane , organic chemistry , computer science , operating system
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)