Oxidative conversion of β-hydroxyselenides to epoxides and ketones with meta-chloroperbenzoic acid
S Uemura, K Ohe, N Sugita
Index: Uemura, Sakae; Ohe, Kouichi; Sugita, Nobuyuki Journal of the Chemical Society, Chemical Communications, 1988 , # 2 p. 111 - 112
Full Text: HTML
Citation Number: 12
Abstract
Treatment of (3-hydroxy-primary-alkyl and (3-hydroxy-(3-phenyl-primary-alkyl phenyl selenides with 3-5 equiv. of rneta-chloroperbenzoic acid in methanol or tetrahydrofuran gives the corresponding epoxides and phenyl migrated ketones, respectively, in high yields. ... In sharp contrast to the well known selenoxide elimination leading to alkenes, treatment of alkyl phenyl selenides with an excess of meta-chloroperbenzoic acid (MCPBA) in alcohols results in a substitution of ...
Related Articles:
[Yu, Ajuan; Li, Jingya; Cui, Mengjun; Wu, Yangjie Synlett, 2007 , # 19 p. 3063 - 3067]
[Tetrahedron, , vol. 67, # 12 p. 2305 - 2312]
A structure–activity relationship study on the Wacker oxidation of stilbenes at ambient condition
[Darabi, Hossein Reza; Mirzakhani, Mohsen; Aghapoor, Kioumars; Jadidi, Khosrow; Faraji, Laleh; Sakhaee, Nader Journal of Organometallic Chemistry, 2013 , vol. 740, p. 131 - 134]
[Wang, Dawei; Cai, Rong; Sharma, Sripadh; Jirak, James; Thummanapelli, Sravan K.; Akhmedov, Novruz G.; Zhang, Hui; Liu, Xingbo; Petersen, Jeffrey L.; Shi, Xiaodong Journal of the American Chemical Society, 2012 , vol. 134, # 21 p. 9012 - 9019]
[Hajipour; Mallakpour; Backnejad Synthetic Communications, 2000 , vol. 30, # 21 p. 3855 - 3864]