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.
View MoreGuangzhou Reachin Chemical Co., Ltd
Contact:+86-20-37087379 ext.604
Address:A122C-1, Tianyuan Plaza, 401 Tianyuan Rd., Tianhe, Guangzhou, China
Anhui Biochem United Pharmaceutical Co., Ltd.
Contact:0086 551 5167062 / 5228268
Address:No. 30 Hongfeng Road, Hi-Tech Development Zone, Hefei (230088), China
SJZ Chenghui Chemical Co., Ltd.
Contact:86-311-87713916
Address:no.368 youyi north avenue
China Synchem Technology Co.,Ltd
website:http://www.cnsynchem.com
Contact:+86-0552-4929311
Address:No.217 Daqing Road
Shanghai Longjin Metallic Material Co., Ltd.
website:http://www.shlongjin.cn/
Contact:021-56517503,56502257
Address:No.16, Lane 555, Chengyin Road, Shanghai
Doi:10.1016/j.tetlet.2009.02.007
(2009)Doi:10.1021/ja01137a010
(1952)Doi:10.1016/S0040-4039(97)00920-9
(1997)Doi:10.1021/ja9713845
(1998)Doi:10.1039/AN9608500371
(1960)Doi:10.1002/anie.201909922
(2019)