Journal of the Chemical Society. Perkin Transactions 2 (2001) p. 2505 - 2509 (1996)
Update date:2022-08-12
Topics:
Gobbi, Alessandro
Landini, Dario
Maia, Angelamaria
Penso, Michele
Cation electrophilic catalysis has been studied in nucleophilic substitution reactions of octyl methanesulfonate (1) promoted by complexes of macrocyclic polyethers 2-5 with alkali and alkaline-earth metal salts in chlorobenzene. The catalytic effect increases with increasing Lewis acid character of the cation, in the order Cs+ ～ Rb+ ～ K+ < Na+ < Li+ and Ba2+ < Sr2+ < Ca2+, and is mainly related to the ability of the polyether to shield the metal ion charge. Kinetic data clearly indicate that crown ethers 2-4 allow the metal ion participation in the activation process, whereas the cryptand [2.2.2,C10] (5), which more effectively binds the cation, inhibits catalysis. The lower reactivity of the complexes of alkaline-earth metal salts with both crown ethers and cryptands is most likely due to a higher interaction of the divalent cation with the anion in the ion-pair.
View More
Shanghai Forever Synthesis Co.,Ltd.
Contact:021-61124658
Address:Zhoukang Road,Pudong New District,Shanghai,China
Contact:+86-519-86623222
Address:29F/D, 99 Yanling West Road, Changzhou, Jiangsu, China
Shandong Xiangde Biotechnology Co., Ltd
Contact:+86 -15066639877
Address:Sanba street
Nanjing Chemical Material Corp.(NCMC)
website:http://www.njchemm.com
Contact:0086-25-83172879
Address:B12 Technology and Innovation Building, Nanjing Tech University, No.5 New Model Road
Guangzhou Swan Chemical Co., Ltd.
Contact:+86-20-31075659
Address:NO.301, Hong ba fang investment BLDG 1,Guan chong village,Shiqi town,Panyu district,Guangzhou
Doi:10.1002/jccs.201200628
(2013)Doi:10.1039/c6dt01330a
(2016)Doi:10.1021/ja210703y
(2012)Doi:10.1021/ol052160r
(2005)Doi:10.1016/j.jorganchem.2007.10.008
(2008)Doi:10.1002/anie.201707491
(2017)
