Summary
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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Naturally occurring 3-hydroxy flavanones are specified by their trivial names and the synthetic ones by the method of preparation.
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Mahesh, V.B., Seshadri, T.R. Stereochemistry of 3-hydroxy flavanones. Proc. Indian Acad. Sci. 41, 210–223 (1955). https://doi.org/10.1007/BF03047207
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DOI: https://doi.org/10.1007/BF03047207