Abstract

A number of 3-hydroxy flavanones occur in nature and several have been obtained using a number of synthetic methods. Though they behave generally in the same way when subjected to drastic methods of dehydrogenation or dehydration, those obtained by substitution of flavanones in the 3-position seem to differ markedly from others in their reactions towards mild reagents such as dilute sulphuric acid and iodine. This is attributed to stereo-chemical differences. In this particular synthetic method the 3-hydroxyl is axial (H2O elimination easy) whereas in the others it is equatorial (H2 elimination easy). In flavanones substitution of the axially disposed C-H is the favoured one because it is sterically unhindered.

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