The bicyclo[2.2.1]heptan-2,5-diols

Add time:07/28/2019    Source:sciencedirect.com

Two independent recent synthetic routes to byciclo[2.2.1]heptan-exo-2-endo-5-diol (I) have been described by Henbest and Toivonen. The products were clearly different. Re-examination of this discrepancy reveals that the product described by Henbest was essentially pure I, but that Toivonen's product was a mixture containing the previously uncharacterized 2-exo-5-exo isomer (II) and I in about a 2:3 ratio. Both of these diols can be converted to bicyclo[2.2.1]heptan-2,5-dione (IV), which is reduced by lithium aluminum tri-t-butoxy hydride to the third possible 2,5-diol, the 2-endo-5-endo isomer III.

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