Journal of the Chemical Society. Perkin transactions I p. 1009 - 1027 (1983)
Update date:2022-08-05
Topics: Catalyst Mechanism Experimental Base catalysed rearrangements Ylide intermediates
Ollis, W. David
Rey, Max
Sutherland, Ian O.
The Stevens <1,2> rearrangement of acyl-stabilised ammonium ylides has been investigated with regard to stereoselectivity, intramolecularity and the formation of products in addition to the <1,2> rearrangement product.A detailed study of the effects of reaction conditions upon the rearrangement of the ylide derived from the salt (13) has shown that the stereoselectivity (retention of the configuration of the chiral migrating group) and intramolecularity decrease as solvent viscosity decreases.The rearrangement of the salt (13) in water at 0 deg C is essentially intramolecular with virtually complete retention of the configuration of the migrating group.These results, together with the isolation of products that can be rationalised on the basis of random free-radical coupling, indicate that the <1,2> rearrangement of acyl-stabilised ammonium ylides normally involves a radical pair mechanism.
View MoreLianYunGang Chiral Chemical(CHINA) CO.,LTD
Contact:+86-518-83616958 +86-519-82884848
Address:LianYunGang Chemical Industry Park (JiangSu)
Contact:86-551-63540590
Address:No 1388 Furong Rd., Hefei, Anhui, China
Contact:+86-27-67841589
Address:Add: 999 Gaoxin Road, Donghu New Technology Development Zone, Wuhan City, Hubei, China
Guangzhou Reachin Chemical Co., Ltd
Contact:+86-20-37087379 ext.604
Address:A122C-1, Tianyuan Plaza, 401 Tianyuan Rd., Tianhe, Guangzhou, China
Liao Cheng All Win Chemicals Co.,LTD
Contact:86+0635-2991582
Address:Room 402,Unit 1,No.27 building.Zhong tong shi dai haoyuan,liaocheng city,Shan dong Province.China
Doi:10.1021/acs.jmedchem.7b01562
(2017)Doi:10.1016/j.bmc.2005.07.075
(2006)Doi:10.1021/jm00367a006
(1984)Doi:10.1021/ja046901f
(2004)Doi:10.1016/S0040-4020(01)91918-0
(1983)Doi:10.1016/j.chempr.2020.09.021
(2020)
