Journal of Organic Chemistry p. 3403 - 3408 (1982)
Update date:2022-08-02
Topics:
Freeman, Fillmore
Angeletakis, Christos N.
Maricich, Tom J.
At -30 deg C under nitrogen in CDCl3 the m-chloroperoxybenzoic acid (MCPBA) oxidation of S-phenyl 2,2-dimethylpropanethiosulfinate (18) leads to S-(2,2-dimethylpropyl) 2,2-dimethylpropanethiosulfonate (9), 18, S-phenyl 2,2-dimethylpropanethiosulfonate (19), 2,2-dimethylpropanesulfinic acid (20), and 2,2-dimethylpropanesulfonic acid (21).These products are consistent with attack by MCPBA at the sulfenyl sulfur atom of 18 to give α-disulfoxides 28 and at the sulfinyl sulfur atom of 18 to give 19.At 24 deg C, 18 reacts with 20 to give 19 and 2,2-dimethylpropanesulfenicacid (33), which dimerizes to S-(2,2-dimethylpropyl) 2,2-dimethylpropanethiosulfinate (5).Possible concerted, ionic, and radical mechanisms for these observations are discussed.
View MoreContact:86-21-50966856
Address:Building 5,300 Chuanzhan Road,Pudong New District,Shanghai
Jinan Decheng Hemu Medical Technology Co.,Ltd.
Contact:+86-531-68650525
Address:NO.554 Zhengfeng Road High-new Technology Development Zone
Nanjing Chemipioneer Pharma&Tech Co.,Ltd
website:http://www.chemipioneer.com.cn
Contact:+86-25-52685700
Address:Room 305,A Block,Biological-Medicine Building,Business Start-up Center,Xin-ke 1st Road, High-tech development zone,Nanjing city,Jiangsu Province, China
He Bei Shun Er Chemical Co., LTD.
Contact:86-0311-86996932/86860168
Address:No 18,North street
ClickChem Technology Co., Limited
Contact:+86-0310-6519966/0531-52893837
Address:No.750 Shunhua Road, High-Tech Zone, Jinan city, Shandong China
Doi:10.1021/jo01351a062
(1961)Doi:10.1016/S0040-4039(02)00784-0
(2002)Doi:10.1021/jo0300800
(2003)Doi:10.1021/ol026378e
(2002)Doi:10.1016/j.bmc.2005.05.043
(2005)Doi:10.1002/1099-0682(200207)2002:7<1657::AID-EJIC1657>3.0.CO;2-W
(2002)