Extending the haloform reaction to non-methyl ketones: Oxidative cleavage of cycloalkanones to dicarboxylic acids using sodium hypochlorite under phase transfer catalysis conditions

Tetrahedron

Volumn 52, Issue 43, 1996, Pages 13641-13648

  Rothenberg, Gadi ^a   Sasson, Yoel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030597004     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00816-2     Document Type: Article

References (32)

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23. - are present, the chlorination of 9 is faster than the hydrolysis reaction to 2a. However, the yield of 2 can be maximized by performing the reaction at a constant pH of 12, where [HOCl] is negligible.
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28. 16. Traces (less than 1%) of 3 were detected when using 2 as a substrate.
29. 17. Although 6 can undergo under certain conditions a reaction known as the Favorskii rearrangement (March, J. Advanced Organic Chemistry; John Wiley and Sons, Inc.: New York, 1992; pp. 1080-1083) we do not believe this to be the case here, as there is neither an alkoxide ion present, nor were any traces of the rearrangement products detected.
30. 4 can be used to obtain dicarboxylic acids from diols and diketones, going through intermediates of the α,β-dioxo and α,β,γ-trioxo variety. See, for example, Wolfrom, M.L.; Bobbitt, J.M. J. Am. Chem. Soc. 1956, 78 2489.
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32. 20. CAUTION! Care should be taken at this stage as some chlorine and carbon dioxide is released from the mixture.