The tetrabutylammonium salt of isotopically chiral phenyl phosphate was heated in the polar aprotic solvent acetonitrile containing
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The tetrabutylammonium salt of isotopically chiral phenyl phosphate was heated in the polar aprotic solvent acetonitrile containing excess tert-butyl alcohol, and isotopically substituted tert-butyl phosphate was isolated. An analysis of its stereochemistry showed that it was completely racemic.
(See Fig. P25.31) Explain this result with a mechanism.
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Racemization of the product suggests that a single inve...View the full answer
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