From: David.K.O-Dell-1 (dko$##$ou.edu)
Date: Tue Nov 09 1999 - 15:28:43 EST
>
Joseph Swaroop Mathen Wrote:
>
>
> does any one know how to synthesise the oxime of chalcone ? the usual
> combination of ketone, hydroxylamine hydrochloride ane pyridine does
> not go to completion as observed in the case of benzalacetone.
> thank you and with best regards
> swaroop
>
Swaroop,
According to Durga Nath Dhar's short book The Chemistry of Chalcones and
Related Compounds (Wiley 1981), under basic conditions reaction of chalcone
with hydroxylamine gives 3,5-Diphenylisoxazoline. Presumably this is formed
via the syn-oxime which then undergoes cyclization to the isoxazoline. You
might try acidic conditions; the reaction may not be as fast, but the
cyclization might be inhibited. Or try these references:
Auwers, K. V.; Seyfried, M., Annalen, 484, 178, (1930).
Auwers, K.V. ; Muller, H., J. Prakt. Chem. 137, 57, (1933).
Meisenheimer, J., and Campbell, N., Annalen, 539, 93 (1939)
Samula, K., Roczniki Chem., 45 2063 (1971).
Henrich, F., Annalen, 351, 172.
Hope this helps,
David O'Dell
University of Oklahoma
Dept. Of Chemistry
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