Journal of Organic Chemistry p. 2965 - 2968 (1985)
Update date:2022-09-26
Topics:
Cohen, Theodore
Kosarych, Zenyk
Suzuki, Kunio
Yu, Lin-Chen
2-<(Phenylthio)methyl>cyclopent-2-en-1-one (2), which is readily available by the reaction of 2-cyclopentenone with thiophenol, formaldehyde, and triethylamine, is transformed, in high yield and moderate conversion by treatment with (trimethylsilyl)methyl triflate, cesium fluoride, and benzaldehyde, to 2-methylene-3-<(phenylthio)methyl>cyclopentanone (3), which, by the use of trichloroisocyanuric acid (Chloreal), can be quantitatively dichlorinated on the sulfur-bearing carbon atom to 3-<(phenylthio)dichloromethyl>-2-methylenecyclopentanone (4).This dichloro thioether could be hydrolyzed in good yield to a mixture of sarkomycin phenyl thio ester (5) and sarkomycin (6), containing mainly the former; an additional small amount of sarkomycin can be obtained by hydrolysis of the thio ester in the presence of silver trifluoroacetate and benzhydrol.This procedure represents one of the shortest extant syntheses of sarkomycin and a sarkomycin ester.Model studies of the dichlorination of n-octyl phenyl sulfide (8) to 1-(phenylthio)-1,1-dichlorooctane (9) and various transformations of the latter are also reported.
View MoreAnhui Jiatiansen Agrochemical Co.,Ltd
Contact:15366811918
Address:chemical industrial park,xiangyu town,dongzhi county,anhui,china
Longhui qunfeng Chemical Co., Ltd
Contact:86-731-82173407
Address:South-east Industrial Park, Longhui County, Hunan Province, China
Shanghai Hongbang Medical Technology CO.,. Ltd
Contact:13671516988 /18917636693
Address:Room1, No67 Building, Yongde Road369, Wujing Town, Minhang Districy, Shanghai CIty, China.
Jiaxing Carry Bio-Chem Technology Co.,Ltd
website:http://www.carrybiotech.com
Contact:0573-82788958
Address:Add.Fl 3th, Pharm Vally,Kaichuang Rd, Xiuzhou District, Jiaxing, Zhejiang,314031,China
DACHANG OLEOCHEMICALS CO.,LTD.
Contact:0543-2875999
Address:Xingbo 10 Road,EDZ,Boxing Town,Shandong
Doi:10.1021/jo00149a016
(1983)Doi:10.4039/Ent133409-3
(1959)Doi:10.1021/jo00151a030
(1983)Doi:10.1016/0040-4039(91)80669-W
(1991)Doi:10.1016/S0040-4020(99)00119-2
(1999)Doi:10.1002/hlca.200490264
(2004)