Journal of Organic Chemistry p. 1037 - 1040 (1985)
Update date:2022-07-29
Topics:
Russell, Glen A.
Herold, Lourdes Lucas
Free-radical chain substitution reactions of allyltributylstannane were observed with PhSSPh, PhCH2SSCH2Ph, PhSeSePh, PhSO2Cl, n-PrSO2Cl, or CCl3SO2Cl, where the attacking radicals leading to allylic rearrangement with displacement of Bu3Sn(radical) were PhS(radical), PhCH2S(radical), PhSe(radical), PhSO2(radical), n-PrSO2(radical), and CCl3(radical), respectively.Allylic rearrangement was also observed in the SH2' reaction of crotyltributylstannane with PhSSPh, PhCH2SSCH2Ph, PhSO2Cl, or n-PrSO2Cl.Propargyltriphenylstannane underwent SH2' substitution to form the allenic substitution products with PhSO2Cl, n-PrSO2Cl, CCl4, and CHCl3 while 2-butynyltriphenylstannane formed the 1,2-butadiene with PhSO2Cl or n-PrSO2Cl.Reaction of (1-cyclohexenyloxy)tributylstannane with CCl4 or BrCCl3 formed α-(trichloromethyl)cyclohexanone.With HCBr3 the initially formed α-(dibromomethyl)cyclohexanone readily underwent dehydrobromination to form α-(bromomethylene)cyclohexanone. <(2-Methyl-1-propenyl)oxy>tributylstannane formed α-(trichloromethyl)isobutyraldehyde with CCl4 or BrCCl3.Reaction with HCBr3 gave a mixture of α-(dibromomethyl)isobutyraldehyde and 1-(dibromomethyl)-2,2-dimethyloxirane.
View MoreHangzhou Zyter Biological & Chemical Technology Co., Ltd.
website:http://www.zyterpharm.com
Contact:+86-18858184290
Address:West Wenyi Road, Cangqian, Yuhang
Anhui Eapearl Chemical Co., Ltd.
Contact:86-562-5858458
Address:358 South Huaihe Road
Xiamen Huasing Chemicals Co.Ltd.
Contact:0086-592-6228397
Address:NO.24, Xinglin North 2nd Road,Jimei district
Tianjin Jingye Fine Chemicals Co., Ltd.
Contact:+86-15722078107; +86-22-26911407
Address:Bohua Fine Chemicals Base of Petrochemical Industry Park, Nanhuan Road, Dagang District, Tianjin, 300271, P. R. China
MS( MAOSHENG )Chemical CO.,LTD
Contact:+86-519-82726678.82726378
Address:TAOXI INDUSTRY ZONE JINTAN
Doi:10.1139/v63-117
(1963)Doi:10.1016/j.bmc.2012.05.062
(2012)Doi:10.1021/jo01029a032
(1964)Doi:10.1021/jo801046j
(2008)Doi:10.1021/jo01036a015
(1963)Doi:10.1016/j.bioorg.2020.104320
(2020)