Helvetica Chimica Acta p. 587 - 592 (1987)
Update date:2022-08-11
Topics:
Burger, Ulrich
Erne-Zellweger, Dominique
Mayerl, Christa
The title ester 5 is shown to undergo C-C bond cleavage under the conditions of basic ester hydrolysis (KOH/EtOH) with formation of potassium ethyl carbonate (6) and the tautomeric methylcyclopentadienes 7 and 8.In contrast, porcine liver esterase (PLE, EC 3.1.1.1) cleanly hydrolyses 5 to give the isolable 1-methyl-2,4-cyclopentadiene-1-carboxylic acid (13).The latter undergoes thermal dimerization with conservation of the geminal-substitution pattern.The configuration of the Diels-Alder adduct 17 is ascertained by it photochemical transformation into bishomocubane dicarboxylic acid 12, easily distinguished by its C2 symmetry.Under the conditions of acid-catalyzed hydrolysis, dimerization of ester 5 and polymerization prevail, unless low acidic concentration is used.The dimer 9 of 5 has one ester function that is reluctant to undergo basic hydrolysis.
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