Journal of Organic Chemistry p. 2590 - 2598 (1983)
Update date:2022-08-04
Topics:
Dave, Vinod
Warnhoff, E. W.
A method has been developed for the regiospecific homologation of unhindered unsymmetrical ketones.The procedure consists of preparation of a pure α-halo ketone, reaction of this derivative with ethyl diazoacetate and boron trifluoride etherate, removal of the halogen by zinc reduction, and finally decarbethoxylation with water at 230 deg C or with CaCl2*2H2O in dimethyl sulfoxide at 150 deg C.The method depends on the electron-withdrawing power of the α-halogen to prevent the migration of the attached carbon.A-Homo steroid ketones are most conveniently prepared by this method.The reaction of α-acetoxy ketones with ethyl diazoacetate also leads mainly to migration of the unsubstituted α'-carbon atom.
View Moreshandong lukang animal & plant drug trading co.,ltd.
Contact:15853765968
Address:floor 9, lukang ,jingying building,#173,taibai building west road,jining city,shandong,china
Contact:+86-579-85206992
Address:No 451 chouzhou north road ,room 1106 int'l business center , yiwu ,china
NINGBO YINZHOU PRECISE COLOR CO.,LTD.
Contact:86-574-88139809 86-574-83033159
Address:Qiming Road,Yinzhou,Ningbo,China
Contact:+86-577-65618087-605
Address:Room 402, Unit 4 Xinhu Bldg. Waitan Ruian City, Zhejiang China.
Contact:+86 755 26588093
Address:No.9 Linkong West Street, Hengdian Street, Huangpi District, Wuhan City, China.
Doi:10.1021/jo01019a019
(1965)Doi:10.1016/S0040-4020(01)81014-0
(1989)Doi:10.1021/jo016187+
(2002)Doi:10.1021/jo00013a041
(1991)Doi:10.1021/jo00939a021
(1974)Doi:10.1021/ja01182a070
(1948)
