Synthesis of spiro oxirane derivatives of the decahydroquinoline series
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It was established that 1-methyl-, 1-ethyl-, 1,2-dimethyl-, and 1,2,2-trimethyl-4-oxiranyl-trans-decahydro-4-quinolols undergo isomerization under the influence of aqueous or alcohol solutions of sodium hydroxide, barium hydroxide, and thiourea with migration of the oxide ring to give the corresponding spiro epoxy compounds. A comparison of the IR spectra of the spiro epoxy compounds with the spectra of alternative products, viz., the corresponding keto alcohols, showed that keto alcohols are not formed under the given reaction conditions. The indicated conclusions are confirmed by the IR, PMR, and mass spectra.
KeywordsAlcohol Migration Hydroxide Mass Spectrum Epoxy
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