110977-38-3Relevant academic research and scientific papers
Ring-Expansion of Bridgehead Aldehydes with 1-Adamantanecarbonyl Cation or Benzoyl Trifluoromethanesulfonate: A New Route to Bicyclic and Tricyclic 1,2-Diols
Takeuchi, Ken'ichi,Kitagawa, Itsuko,Akiyama, Fumio,Shibata, Tadashi,Kato, Midori,Okamoto, Kunio
, p. 612 - 615 (1987)
Acylation of bridgehead aldehydes with 1-adamantanecarbonyl cation generated from 1-adamantyl cation and carbon monoxide, or with benzoyl trifluoromethanesulfonate, in the presence of trifluoromethanesulfonic acid causes ring-expansion of the aldehydes by one carbon atom.Work-up of the reaction mixture with water affords a bridgehead alcohol containing the acyloxy group on the vicinal carbon, which on saponification gives a vicinal glycol in good overall yields.For example, bicycloheptane-1-carbaldehyde gives bicyclooctane-1,2-diol which is not easily accessible by the other methods.
