Journal article

Publication year: 2006

Pages: 8532-8540

Journal: The Journal of Organic Chemistry

Volume number: 71

Issue number: 22

DOI Link: https://doi.org/10.1021/jo061561x

Publisher: American Chemical Society

Abstract: 

To model the chemical properties of the hydrogen-terminated nanodiamond
{111} and {110} surfaces, the functionalizations of the higher
diamondoid [1(2,3)4]pentamantane were studied. [1(2,3)4]Pentamantane
reacts selectively with neat bromine to give the medial 2-mono- and
2,4-disubstitution products. In contrast, oxidation with nitric acid as
well as single-electron-transfer oxidation involving the
[1(2,3)4]pentamantane radical cation results in apical C⁷-substitutions.
This substitution pattern dominates in the free-radical bromination
under phase-transfer catalytic conditions that gives a mixture of 7- and
2-bromo[1(2,3)4]pentamantane in a 95:5 ratio. Replacement of the
functional groups in [1(2,3)4]pentamantane occurs without isomerization.
This was demonstrated for the interconversions of the bromo and hydroxy
derivatives as well as for the preparation of
[1(2,3)4]pentamantyl-7-thiol from 7-hydroxy[1(2,3)4]pentamantane. Thus,
the selective functionalization of hydrogen-terminated nanodiamonds is
possible by means of reactions with common electrophiles−oxidizers.

Harvard Citation style: Fokin, A., Schreiner, P., Fokina, N., Tkachenko, B., Hausmann, H., Serafin, M., et al. (2006) Reactivity of [1(2,3)4]Pentamantane (Td-Pentamantane): A Nanoscale Model of Diamond, The Journal of Organic Chemistry, 71(22), pp. 8532-8540. https://doi.org/10.1021/jo061561x

APA Citation style: Fokin, A., Schreiner, P., Fokina, N., Tkachenko, B., Hausmann, H., Serafin, M., dahl, J., Liu, S., & Carlson, R. (2006). Reactivity of [1(2,3)4]Pentamantane (Td-Pentamantane): A Nanoscale Model of Diamond. The Journal of Organic Chemistry. 71(22), 8532-8540. https://doi.org/10.1021/jo061561x