Tetrahedron p. 10843 - 10854 (1993)
Update date:2022-08-06
Topics:
Bennetau, Bernard
Rajarison, Florent
Dunogues, Jacques
Babin, Pierre
Functionalisation in 2 position of benzenes 1,3-disubstituted by para-directing groups has been investigated, involving 2-trimethylsilylated intermediates when the classical methods (particularly these involving the anion in 2 position) are ineffective. Thus 2-trimethylsilyl derivatives of 1,3-dihalo- or 1,3-dimethoxybenzene have been prepared in good yields. Their conversion into the corresponding 1,2,3-trisubstituted benzenes has been conveniently performed upon acetylation, iodination or sulfonation, except in the case of the sulfonation of the 1,3-dimethoxylated compound in which the ipso effect of the silyl group is surpassed by the directing effect of the methoxy substituents. In contrast, whith the same substrate, cyanation in position 2 was successfully carried out using chlorosulfonyl isocyanate: to our knowledge this reaction is the first example of substitution of a trimethylsilyl by a cyano group in the aromatic series.
SHIJIAZHUANG HENRYTE CHEMICALS CO,.LTD(expird)
Contact:+86-311-85208698 311-80837698
Address:NO.166, yuhua west road, SHIJIAZHUANG, China
Changsha Kamer Essence and Flavor Co.,Ltd
Contact:86-731-89832270
Address:No.327 Kangnin Road Changsha Bio Information Industry Park, Changsha city, Hunan province
Contact:86-10-62983737; +86-10-51287608
Address:4/F Building C, 2 Shangdi Xinxi Road
Cerametek Materials（ShenZhen）Co., Ltd.
Contact:+86-755-2324.2554
Address:A3-#9, YongChuan Street, Suite 501
website:http://www.honourchina.com
Contact:+86-592-8316013
Address:Room 416, Fortune Harbour Building, #398 Jiahe Road, Huli District, Xiamen, Fujian, China
Doi:10.1002/ejoc.200600835
(2007)Doi:10.1039/d0ra06519f
(2020)Doi:10.1021/jm00351a016
(1982)Doi:10.1016/j.bmc.2010.01.003
(2010)Doi:10.1016/0008-6215(84)85405-1
(1984)Doi:10.1021/jo034739d
(2003)
