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Reduktone von Tetron‐, Thiotetron‐ und Tetramsäuren, II. Reduktone durch Rhodium‐katalysierte Zersetzung von Diazoverbindungen
Author(s) -
Stachel HansDietrich,
Poschenrieder Hermann,
Redlin Jutta,
Schachtner Josef,
Zeitler Klaus
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940205
Subject(s) - chemistry , diazomethane , rhodium , diazo , medicinal chemistry , catalysis , decomposition , organic chemistry
Reductones of Tetronic, Thiotetronic and Tetramic Acids, II. – Reductones by Rhodium‐Catalyzed Decomposition of Diazo Compounds The diazoketones 2 have been synthesized by diazo transfer reaction with 2‐azido‐3‐ethylbenzthiazolium tetrafluoroborate. The rhodium‐catalyzed decomposition of compounds 2 in tert ‐butyl alcohol at 130°C furnishes the reductone monoethers 3 and after deprotection the aci ‐reductones 4 . Methylation of compounds 4 with diazomethane proceeds stepwise leading first to the monoethers 5 and then to the diethers 6 . The thiolactone 4b and even more the lactams 4c and 4d are stronger reducing agents than the lactone 4a .