1994
DOI: 10.1246/bcsj.67.1091
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Oxidative Deoximation with Sodium Hypochlorite

Abstract: A simple and convenient procedure for the deoximation with 0.5 M aqueous hypochlorite at ambient temperature is reported. Ketoximes yielded ketones quantitatively and aldoximes yielded aldehydes only at pH 5—7 or mixture of aldehydes and carboxylic acids at pH 10—11.

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Cited by 33 publications
(13 citation statements)
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“…In organic synthesis, aldehyde groups can be protected as oximes, [14] which are rapidly deprotected by hypochlorite under mild conditions (i.e., at ambient temperature) (Scheme 1). [15] Abstract: In this work, we have successfully provided a novel strategy for the rational design and synthesis of a ratiometric fluorescent probe for hypochlorite. The strategy is based on the deoximation reaction, which has not yet been used in the fluorescent hypochlorite probe design.…”
Section: à5mentioning
confidence: 99%
“…In organic synthesis, aldehyde groups can be protected as oximes, [14] which are rapidly deprotected by hypochlorite under mild conditions (i.e., at ambient temperature) (Scheme 1). [15] Abstract: In this work, we have successfully provided a novel strategy for the rational design and synthesis of a ratiometric fluorescent probe for hypochlorite. The strategy is based on the deoximation reaction, which has not yet been used in the fluorescent hypochlorite probe design.…”
Section: à5mentioning
confidence: 99%
“…[1][2][3] There has been great interest in the development of mild techniques for the conversion of oximes into their corresponding carbonyl compounds. [4,5] A number of methods have been developed for the regeneration of carbonyl compounds from hydrazones, [6][7][8] but most of these methods suffer some disadvantages such as large reaction time, higher reflux temperature, difficulties in isolation of products and low yield.…”
Section: Introductionmentioning
confidence: 99%
“…Therefore, there has been considerable interest in the development of mild techniques for the conversion of oximes into their corresponding carbonyl compounds. [5][6][7][8][9][10] Although some of the known methods are carried out under mild reaction conditions, most of them require drastic conditions, high temperature, long reaction times, toxic or not-readily available reagents; they need to be freshly prepared, and have tedious work-up procedures. Little attention has been paid to the regeneration of carbonyl compounds from hydrazones, semicarbazones and azines.…”
Section: Introductionmentioning
confidence: 99%