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Synthesis of a Nitro Analogue of Plakoric Acid †
Author(s) -
Zhang Qi,
Jin HongXia,
Liu HeHua,
Wu YiKang
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690222
Subject(s) - chemistry , hydroperoxyl , boron trifluoride , nitro , intramolecular force , medicinal chemistry , hydrogen peroxide , double bond , reagent , ether , substrate (aquarium) , yield (engineering) , organic chemistry , catalysis , radical , alkyl , oceanography , materials science , geology , metallurgy
Synthesis of a nitro analogue of plakoric acid is presented. The peroxy bond was incorporated into the substrate structure through a boron trifluoride etherate catalyzed methoxy‐hydroperoxy group partial exchange reaction in diethyl ether with urea‐hydrogen peroxide complex (UHP, a commercially available solid reagent) as the source of the hydrogen peroxide. Under the given conditions, only one of the two methoxyl groups underwent the MeO–OOH exchange and the resulting hydroperoxy hemiketal proceeded directly to the end product through an intramolecular Michael addition of the hydroperoxyl group to the nitro group activated carbon‐carbon double bond.