Journal article

Publication year: 2014

Pages: 1861-1866

Journal: The Journal of Organic Chemistry

Volume number: 79

Issue number: 4

DOI Link: https://doi.org/10.1021/jo4026594

Publisher: American Chemical Society

Abstract: 

Homodiamantane bromination and nitroxylation are accompanied by
contraction of the seven-membered ring to give the corresponding
substituted 1-diamantylmethyl derivatives. In contrast, CH-bond
hydroxylations with dimethyldioxirane retain the cage and give both
apically and medially substituted homodiamantanes. The product ratios
are in accord with the barriers for the oxygen insertion computed with
density functional theory methods only if solvation is included through a
polarizable continuum model. B3LYP-D3 and M06-2X computations with a
6-31G(d,p) basis set on the oligomeric van der Waals complexes predict
the potential of homodiamantane derivatives for surface modifications
with conformationally slightly flexible diamondoid homologues.

Harvard Citation style: Fokin, A., Zhuk, T., Pashenko, A., Osipov, V., Gunchenko, P., Serafin, M., et al. (2014) Functionalization of Homodiamantane: Oxygen Insertion Reactions without Rearrangement with Dimethyldioxirane, The Journal of Organic Chemistry, 79(4), pp. 1861-1866. https://doi.org/10.1021/jo4026594

APA Citation style: Fokin, A., Zhuk, T., Pashenko, A., Osipov, V., Gunchenko, P., Serafin, M., & Schreiner, P. (2014). Functionalization of Homodiamantane: Oxygen Insertion Reactions without Rearrangement with Dimethyldioxirane. The Journal of Organic Chemistry. 79(4), 1861-1866. https://doi.org/10.1021/jo4026594