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Contribution à l'étude des N-Halogènimides II (1). La N-Chlorosuccinimide

✍ Scribed by M. F. Hebbelynck; R. H. Martin


Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
681 KB
Volume
60
Category
Article
ISSN
0037-9646

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✦ Synopsis


Contribution i i 1'6tude des N-Halog6nimides I1 ( 1 ) . La N-Chlorosuccinimide M. F. HEBBELYNCK e t R. H. MARTIN (Bruxelles) SUMMARY. -We have studied the action of N-chlorosuccinimide, in anhydrous organic solvents, on derivatives of the following general formulae : Ar-CHIX and Ar-CH /x .

\ Y 1) Using this technique, we have oxidized benzyl alcohol into benzaldehyde in 74 % yield. We have also oxidized a-and P-naphthyl- carbinol, 0-, m-and p-tolylcarbinol, phthalyl alcohol, benzhydrol and n-butylphenylcarbinol into the corresponding aldehydes and ketones.

  1. N-chlorosuccinimide reacts violently with bemylamine to give, after hydrolysis, benzaldehyde (31 0 4 yield) and benzonitrile (34 yo yield).

  2. Benzyl chloride and benzaldehyde give respectively benzal chloride and benzoyl chloride which have been characterized by hydrolysis to benzaldehyde and benzoic acid.

Dans un premier article, nous avons etudie la substitution d'un atome d'hydrogene du groupe mkthyle fixe sur un noyau aromatique par un atome de chlore au moyen de la N-chlorosuccinimide (l).

Frappes par la reactivite de la N-chlorosuccinimide vis-a-vis du toluene, now avons entrevu la possibilite d'etendre ces chlorurations a d'autres composks aromatiques (1) Pour I voir : M.P. HEBBELYNCK e t R.H. MARTIN, B.ull. Sw.


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