Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines

Direct unequal C–H
bond difunctionalization of phosphorylated
diamantane was achieved in high yield from the corresponding phosphonates.
Reduction of the functionalized phosphonates provides access to novel
primary and secondary alkyl/aryl diamantane phosphines. The prepared
primary diamantyl phosphines are quite air stable compared to their
adamantyl and especially alkyl or aryl analogues. This finding is
corroborated by comparing the singly occupied molecular orbital energy
levels of the corresponding phosphine radical cations obtained by
density functional theory computations.