OXIDATIVE DEOXIMATION WITH H 2 0 2 AND MCM-41 N. Vijayakumari, B. Balakrishna Reddy and Lingaiah Nagarapu* Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad, India. E-mail:yurponihgca nagarapu2@yahoo.co.in Abstract : A simple and mild method of oxidative deoximation with 30%H 2 0 2 and MCM-41 is described. This method is effective for deprotection of ketones and aldehydes. Key words : oxidative deoximation, 30%H 2 0 2 , MCM-41, ketones, aldehydes. A number of carbonyl functional group equivalents are routinely employed in organic synthesis. Oximes are readily available and highly stable derivatives of carbonyl compounds that have been regarded both as protective. 1 Oximes have been used extensively for purification and charecterization of carbonyl compounds. 2 They also provide a viable route to amides from carbonyl equivalents via Beckmann rearrangement. 3 However, the utility of oximes as carbonyl equivalents is limited by the methods employed for their regeneration. Classically they are regenerated by acid hydrolysis under suitable conditions. 4 This process removes hydroxylamine from the equilibrium. There are limits to the scope of this reaction since compounds containing acid sensitive groups cannot be subjected to this hydrolysis. Recently there has been a lot of stress on the oxidative, 5 reductive 6 and microwave irradiation 7 methods for cleavage of deoximation. It has been found that most of the oxidative methods use noncatalytic amount of corrosive and carcinogenic metals such as chromium or expensive catalysts or mostly involve microwave technics. In view of the recent stress on the catalytic processes towards the development of clean and green chemical processes 8 , investigation of new, less hardous chemical oxidants has become a priority for the synthetic organic chemists. Herein, we report the use of a combination of MCM-41 and hydrogen peroxide as a novel reagent system for the oxidative deoximation. Treatment of oxime (both ketoximes and aldoximes) with 30% hydrogen peroxide in acetone, in the presence of 10 mol % of MCM-41 9 " n at ambient temperature afforded the corresponding carbonyl compound. 12 In order to test the generality of the deoximation various types of oximes were subjected to the oxidation in the presence of 10 mol % of MCM-41 and 30% hydrogen peroxide to yield the corresponding carbonyl compounds in moderate to good yields (Table-1) 407 Brought to you by | Purdue University Libraries Authenticated Download Date | 6/7/15 12:27 PM