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Derivate der Oxalyldimalonsäure
Author(s) -
Stachel HansDietrich,
Schorp Matthias,
Maier Ludwig,
Dandl 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.199419941112
Subject(s) - chemistry , saponification , lactone , isomerization , enamine , regioselectivity , ring (chemistry) , derivative (finance) , cleavage (geology) , catalysis , stereochemistry , organic chemistry , geotechnical engineering , fracture (geology) , financial economics , engineering , economics
Derivatives of Oxalyldimalonic Acid Starting with furanone 3 and mesoxalic acid esters, the compounds 8 as monolactones of the title compound have been synthesized. A versatile intermediate is the dioxinone 15 , the masked acylketene 16 . Regioselective partial saponification of 8a led to the diester 8e which was converted into the dilactone 2 . The enamine 8d isomerizes by two pathways. By alkanolate catalysis the γ‐alkylidenetetramic acid 24 was obtained and used to prepare the lactam‐lactone 25 and the dilactam 27 . Thermal isomerization of 8d gave the cyclic tetracarbonylmethane derivative 19 . Ring opening reactions of 19 did not furnish derivatives of the title compound but the isomeric acids 20–23 . Some open‐chain derivatives of oxalylbismalonic acid ( 12, 26 ) were obtained from 8c/8d by lactone cleavage.