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First Isolation of Thione‐Propiolic Acid Adducts − Synthesis of Thiodioxenones
Author(s) -
Okuma Kentaro,
Maekawa Shinobu,
Shibata Shinji,
Shioji Kosei,
Inoue Thoru,
Kurisaki Tsutomu,
Wakita Hisanobu,
Yokomori Yoshinobu
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.200300300
Subject(s) - chemistry , adduct , adamantane , yield (engineering) , organic chemistry , medicinal chemistry , stereochemistry , metallurgy , materials science
Treatment of adamantane‐2‐thione ( 1a ) with propiolic acid ( 2a ) afforded a novel type of cycloadduct, spiro[adamantane‐2,2′‐[1,3]oxathiin]‐6‐one ( 3a ), in quantitative yield. The reaction proceeds through a concerted process, as was confirmed by kinetic analysis. Treatment of 1a with butynoic acid or phenylpropiolic acid gave the corresponding adducts regioselectively. Interestingly, only one isomer was obtained by treatment of thiofenchone with propiolic acid, suggesting that the reaction proceeded stereospecifically. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)