Analogues of chroman-3-spirocyclopropan-4-one, on reduction by sodium borohydride gave, as major product, the chroman-4-ol resulting from hydride attack on the more hindered side of the carbonyl group. The chroman-4-ols were stereoselectively rearranged by acid catalysts to 3-substituted 2H-chromens.
P. Bennett, J. A. Donnelly, D. C. Meaney and P. O'Boyle, J. Chem. Soc., Perkin Trans. 1, 1973, 688 DOI: 10.1039/P19730000688
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