Studies in pyran,its analogs,and related compounds

The lithium aluminum hydride reduction of the ethers and tosylates of chroman-4-one oxime and related compounds has been studied. It has been found that the ethers of the oximes, like the oximes, do not undergo a normal, but rather an anomalous, reduction. The tosylates of the oximes exhibit a higher tendency to undergo anomalous reduction than the corresponding oximes. During the synthesis of the ethers of the oximes it was established that the use of dimethylformamide as the medium for alkylation of the oxime salts helps to suppress the side reaction forming nitrones.For part XXXVII, see 23].