Journal of Organic Chemistry p. 5550 - 5555 (1994)
Update date:2022-09-26
Topics: Derivatives in situ Iodohydrin Bromohydrin Hypohalous Acids H5IO6 NaBrO3 NaHSO3
Masuda, Haruyoshi
Takase, Kiyoshi
Nishio, Masahiro
Hasegawa, Akira
Nishiyama, Yutaka
Ishii, Yasutaka
Hypohydrous acids such as hypoiodous acid (IOH) and hypobromous acid (BrOH) were found to be easily generated from H5IO6 and NaBrO3 in the presence of an appropriate reducing agent such as NaHSO3.Iodohydrin and bromohydrin derivatives were synthesized in good yields from the reaction of a wide variety of organic compounds bearing carbon-carbon double bonds, with H5IO6 or NaBrO3 and NaHSO3.The iodohydroxylation of internal alkenes was achieved with high stereoselectivity to give anti products, although no stereoselectivity was observed in the bromohydroxylation of these alkenes.It was found that allylic alcohols undergo iodohydroxylation in anti-Markovnikov fashion to form iodo diols in good yields.Treatment of alkynes with H5IO6 combined with NaHSO3 afforded the corresponding ketones in fair yields, but the same treatment with NaBrO3 rather than H5IO6 produced the corresponding α,α-dibromo ketones along with small amounts of the dibromoalkenes.
View MoreEngineering Research Center of Pesticide, Heilongjiang Province
Contact:+86-451-86609001
Address:No.74 of Xuefu Road, Nangang District,
AllyChem Co., Ltd., Dalian, China(BBChem)
Contact:+86-411-62313318/62313328
Address:No.5 of Jinbin Road, Jinzhou New District, Dalian City, Liaoning Province, P.R.China
Jiangxi Hito Chemical Co., Ltd.
Contact:+86-792-3170318
Address:No. 6, Tianhong Ave., Xinghuo Industry Park, Yongxiu, Jiujiang, Jiangxi, China
SHANDONG CREDAGRI CHEMICAL CO., LTD.
Contact:+86-531-88872050
Address:ROOM 601A, BUILDING 2, SHUNTAI SQUARE, NO. 2000 SHUNHUA ROAD, HI-TECH DEVELOPMENT ZONE, JINAN, CHINA.
website:http://www.debyesci.com
Contact:+85221376140
Address:Rm. 19C, Lockhart Ctr., 301-307 Lockhart Rd., Wan Chai
Doi:10.1021/ol0614525
(2006)Doi:10.1016/S0022-328X(00)98846-6
(1983)Doi:10.1002/ijch.199700005
(1997)Doi:10.1016/S0040-4039(00)81919-X
(1983)Doi:10.1016/j.tetlet.2005.09.137
(2005)Doi:10.1021/ja056071l
(2005)