Journal of Organic Chemistry p. 3824 - 3835 (2004)
Update date:2022-08-05
Topics:
Della, Ernest W.
Graney, Sean D.
A study of the cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl and 5-methyl-5-hexenyl radicals reveals a unique contrast in the mode of ring closure of the radicals. In the case of the 5-hexenyl radicals, the sulfinyl-substituted species displays unexpected regioselectivity relative to its analogues. Thus, while the α-S- and α-SO2-5-hexenyl radicals give measurable and increasing quantities of 6-endo product, the α-sulfinyl species cyclizes with high selectivity (95.5:4.5) via a 5-exo mode. By contrast, ring closure of the 5-methyl-5-hexenyl radicals is found to give substantially the 6-endo product in all cases. It is the α-sulfonyl-5-methyl-5-hexenyl radical that now exhibits high regioselectivity (97.5:2.5) for 6-endo closure: an illustration of the synthetic value of this observation is the independent synthesis of the model cyclohexyl sulfone 61 in high yield. It is found that ring closure under the conditions employed occurs irreversibly in all cases.
View Morewebsite:http://www.uvchemkleys.com
Contact:+86 21 3868 0172
Address:RM-1203, Ziguang Building, #341 Shangcheng Road, Pudong Dist, Shanghai
Shijiazhuang Haitian Amino Acid Co., Ltd.
Contact:+86-311-88908111
Address:Shijiazhuang Hebei province,China
Contact:+36(21)2523420
Address:Head office: 1102 Budapest, SZENT LASZLO TER 24/B. 1/1., HUNGARY / CHINA
Contact:+86-25-52346955
Address:199,JIANYE ROAD,NANJING,CHINA
Hubei Xinjing New Material Co.,Ltd
Contact:+86-27-83313147
Address:Room402.#Bthe 7th,Headquarter of Huifeng Corporation Qiaokou District,Wuhan China
Doi:10.1016/S0040-4039(00)01306-X
(2000)Doi:10.1248/cpb.48.1634
(2000)Doi:10.1021/ol000289p
(2000)Doi:10.1002/jccs.200400150
(2004)Doi:10.1039/j39710001211
(1971)Doi:10.1055/s-2004-837205
(2005)