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Small Rings, 76 [1] . – Intermediates on the Way to Tetramethyl Cyclopentadienonetetracarboxylate
Author(s) -
Maier Günther,
Wilmes Rolf
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260812
Subject(s) - chemistry , deprotonation , electrophile , yield (engineering) , enol , reagent , medicinal chemistry , acylation , alcohol , salt (chemistry) , dimer , potassium , base (topology) , electrophilic addition , chloride , organic chemistry , catalysis , ion , materials science , metallurgy , mathematical analysis , mathematics
„Potassium salt” 6 , already described by Cookson, reacts with suitable electrophilic reagents to yield the enol esters 8–10 . A base‐catalyzed acylation of the hydroxy group in 8–10 cannot be achieved because deprotonation is immediately followed by a [1,5] ester migration. The same reaction occurs upon heating 8–10 to 80°C, leading to the 1,3‐keto enols 11, 12 , and 14 . Upon treatment of „alcohol” 7 with acetyl chloride only the dimer 3 of cyclopentadienone 2 can be isolated.
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