Journal of Organic Chemistry p. 4609 - 4613 (1984)
Update date:2022-08-04
Topics:
Palacios, Sara M.
Santiago, Ana N.
Rossi, Roberto A.
1-Haloadamantanes and 9-bromotriptycene react under irradiation with diphenylphosphide and diphenylarsenide ions to give the substitution product in good yields. 1-Iodoadamantane (8) also reacts with disodium telluride and disodium selenide under irradiation to give di-1-adamantyl ditelluride and di-1-adamantyl diselenide, respectively. 9,10-Dibromotriptycene with diphenylphosphide gives a good yield of the disubstitution product.It seems that all these reactions occur by the SRN1 mechanism.Substrate 8 reacts under irradiation with carbanionic nucleophiles and diethyl phosphite ion, but the products are adamantane and 1,1'-biadamantyl rather than substitution products.These nucleophiles transfer an electron to 8 to form radical anions which fragment to 1-adamantyl radicals.The radicals are reduced or dimerized.In contrast, amide ions do not react with 8.The ease of the halogen nucleofugality is I > Br > Cl, the same as in the aromatic system.
View MoreHebei Fulong Import & Export Co., Ltd.
Contact:86-311-87795661
Address:15A19 Zhongyuan Building,368 Youyi North Street,Shijiazhuang 050070,China
Shandong Bolode Bio-Technology Co., LTD
Contact:+86-0531-58966870
Address:136 Jingyi Road,Huaiyin District,Jinan,Shandong,China
SEA BRGIHT INDUSTRY CO.,LIMITED
Contact:0086 755 8622 3990
Address:Rm 17B3,GuangCaiXinTianDi Bldg,GuiMiao Rd,NanShan District,Shenzhen,China
Hangzhou Deli Chemical Co.,Ltd.
website:http://www.dlchemical.com
Contact:86 571 28006267
Address:Tangxi Industrial Area, Yuhang District, Hangzhou
website:http://www.mingchem.com/en/index
Contact:0519-85170101-802
Address:Fifth Floor,B of Beihua Buliding,520 Road of Science and Education City,Changwu middle road NO.801,Wujin District,Changzhou,Jiangsu province
Doi:10.1002/chem.200800788
(2008)Doi:10.1016/0040-4020(78)89032-2
(1978)Doi:10.1016/S0040-4020(01)82433-9
(1984)Doi:10.1139/V06-088
(2006)Doi:10.1021/jm00378a011
(1984)Doi:10.1016/j.bmc.2006.10.040
(2007)