Journal article

Publication year: 2006

Pages: 6709-6720

Journal: The Journal of Organic Chemistry

Volume number: 71

Issue number: 18

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/jo052646l

Publisher: American Chemical Society

Abstract: 
The selective functionalizations of the fundamental hydrogen-terminated nanodiamonds triamantane 1, as well as the most symmetrical representative of the tetramantanes (C-2h-[121] tetramantane 2) were elaborated. Electrophilic reagents (Br-2, HNO3) predominantly attack the medial C-H positions of the cages; bromination of 2 gave the medial 2-bromo derivative almost exclusively. Highly selective apical substitution in 1 and 2 is possible either under single-electron-transfer oxidations via hydrocarbon radical cations or through photoacetylation with diacetyl. The mono-and the bis-acetyl derivatives of 1 and 2 were converted through Bayer-Villiger oxidation and subsequent hydrolysis to the respective apical mono-and dihydroxy derivatives. This exceptional synthetic specificity facilitates the transformation of 2, and perhaps larger nanodiamond molecules, into functionalized building blocks needed for a wide range of applications such as nanotechnology.

Harvard Citation style: Schreiner, P., Fokina, N., Tkachenko, B., Hausmann, H., Serafin, M., Dahl, J., et al. (2006) Functionalized nanodiamonds: Triamantane and [121]tetramantane, The Journal of Organic Chemistry, 71(18), pp. 6709-6720. https://doi.org/10.1021/jo052646l

APA Citation style: Schreiner, P., Fokina, N., Tkachenko, B., Hausmann, H., Serafin, M., Dahl, J., Liu, S., Carlson, R., & Fokin, A. (2006). Functionalized nanodiamonds: Triamantane and [121]tetramantane. The Journal of Organic Chemistry. 71(18), 6709-6720. https://doi.org/10.1021/jo052646l