The conformational analyses of substituted methyl styryl ketones and phenyl styryl ketones have been carried out using IR spectroscopy. The split in the C=O bands of these compounds is attributed to the existence of two conformations, viz. s-cis and s-trans, in equilibrium. The methyl styryl ketones exist predominantly in the s-trans form whereas phenyl styryl ketones exist in the s-cis form. In all the ketones studied the proportion of the s-trans form increases with increase in the polarity of the solvent while that of the s-cis form decreases. This shows that the s-trams form is more polar than the s-cis. The field effects between the C--O and C--C groups are found to be electrostatic repulsions which play a dominant role in the determination of the relative stabilities of the s-cis and s-trans forms over the steric effects and the electrostatic attractions between the carbonyl oxygen and the/3carbon.
An efficient synthesis of b-keto-sulfones is described. The reaction of a-haloketones with sodium alkyl/aryl sulphinates in aqueous medium under microwave irradiation afforded the corresponding b-keto-sulfones in excellent yields.
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