Definitive identification of the C‐5 and C‐7 NMR signals of adamantan‐2‐ol

Abstract

Abstract The E ‐ and Z ‐5‐deuterioadamantan‐2‐ols have been synthesized by an unambiguous route. The 13 C NMR spectra show the familiar 1:1:1 splitting of one of the C‐5 or C‐7 signals, thus allowing a definite assignment of the δ‐atoms to be made. This assignment is in accord with the conclusion of Duddeck and Islam. Revised assignments are offered for the reported configurations of the 5‐bromo‐ and ‐chloro‐adamantan‐2‐ols, and several unusual remote deuterium isotope shifts are reported.