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Episulfidation of trans ‐Cyclooctene with an 1,2,4‐Oxadithiolane
Author(s) -
Adam Waldemar,
Bargon Rainer M.,
Mloston Grzegorz
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.200300124
Subject(s) - chemistry , cyclooctene , cycloaddition , sulfur , medicinal chemistry , oxide , stereochemistry , organic chemistry , catalysis
The dipolar cycloaddition of thiobenzophenone S ‐oxide ( 1 ) and 2,2,4,4‐tetramethyl‐3‐thioxocyclobutanone ( 2 ) generates the labile 1,2,4‐oxadithiolane I , which in the presence of trans ‐cyclooctene ( 3 ) affords trans ‐episulfide ( 9 ). In this direct sulfur transfer, the oxathiirane II and/or the dithiirane IV , both derived from the 1,2,4‐oxadithiolane I , are proposed as elusive episulfidating agents. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)