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- W1503729105 abstract "The reaction mechanism and the stereochemistry of an acid-catalyzed allylic rearrangement of four allylic alcohols of 5α-cholestane, the 3-hydroxy-1-enes (5 and 6) and the 1-hydroxy-2-enes (7 and 8), were investigated. The allylic alcohols were heated in dioxane containing a small amount of 1N H2SO4. After the equilibration of the reaction, the products ratio of the four allylic alcohols, 5 : 6 : 7 : 8, was found to be 25 : 20 : 52 : 3, regardless of the stereochemistry of the starting materials. The mechanism of the allylic rearrangement is of SN1 type. The products ratio could be explained in terms of the relative stabilities of the C-1 and C-3 carbocations in the intermediates and the thermodynamic stability of each allylic alcohol." @default.
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- W1503729105 date "1984-01-01" @default.
- W1503729105 modified "2023-09-24" @default.
- W1503729105 title "Studies on the terpenoids and related alicyclic compounds. XXXIII. Acid-catalyzed allylic rearrangement of 1-hydroxy-2-en- and 3-hydroxy-1-en-5.ALPHA.-cholestanes." @default.
- W1503729105 doi "https://doi.org/10.1248/cpb.32.3263" @default.
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