"Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines"

Oana Moncea: Oana Moncea, Maria A. Gunawan, Didier Poinsot, Hélène Cattey, Jonathan Becker, Raisa I. Yurchenko, Ekaterina D. Butova, Heike Hausmann, Marina Šekutor, Andrey A. Fokin, Jean-Cyrille Hierso, and Peter R. Schreiner; Journal of Organic Chemistry, 08/25/16.

Additional Authors: Oana Moncea, Maria A. Gunawan, Didier Poinsot, Hélène Cattey, Jonathan Becker, Raisa I. Yurchenko, Ekaterina D. Butova, Heike Hausmann, Marina Šekutor, Andrey A. Fokin, Jean-Cyrille Hierso, and Peter R. Schreiner

Abstract:

Abstract Image

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.