O-TBS-N-tosylhydroxylamine: A Reagent for Facile Conversion of Alcohols to Oximes

Abstract

A variety of oximes were synthesized from the corresponding alcohols, alkyl halides, or alkyl sulfonates without using external oxidants. With this simple two-step procedure involving substitution with readily available TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared including the ones hardly preparable with conventional procedures.

Synthesis of oxadiazole-2-oxide analogues as potential antischistosomal agents

“…MnO 2 ) failed to give the desired product. Recently, Fukuyama and co-workers reported a mild two-step synthesis of oximes from alcohols via Mitsunobu reaction with N -(tert-butyldimethylsilyloxy)benzenesulfonamide followed by treatment cesium fluoride 25. Gratifyingly, the reaction worked well on our system providing oxime 54 in 42% yield over two steps.…”

A furoxan–amodiaquine hybrid as a potential therapeutic for three parasitic diseases

“…Alternatively, the alcohol was reacted with N -( tert -butyldimethyl-silyloxy) benzenesulfonamide (TBSONHTs) under Mitsunobu conditions, and subsequently treated with cesium fluoride to provide the requisite furoxan oxime 13 . 25,26 Rapid dehydration of the oxime 13 to provide the nitrile 14 was achieved with thionyl chloride, and treatment with HCl in dioxane removed the N -nitroso group to provide the desired furoxan–amodiaquine hybrid 15 (Scheme 1). …”

O-tert-Butyldimethylsilyl-N-tosylhydroxylamine

“…Alkyl bromides, mesylates, and tosylates can be converted to oximes using TsNHOTBS in a one-pot operation (eq 3). 1 In this protocol, the alkyl bromide was exposed to TsNHOTBS and Cs 2 CO 3 in DMF at 60 • C until complete conversion was observed; subsequent addition of CsF to the same reaction vessel produced the oxime in a 91% yield. 1 A similar protocol was implemented with an alkyl mesylate and tosylate, giving 94% and quantitative yields of the oxime, respectively (eq 4).…”