Journal article

Publication year: 2008

Pages: 7789-7792

Journal: The Journal of Organic Chemistry

Volume number: 73

Issue number: 19

DOI Link: https://doi.org/10.1021/jo801321s

Publisher: American Chemical Society

Abstract: 

The monoprotection (desymmetrization) of diamondoid, benzylic, and
ethynyl diols has been achieved using fluorinated alcohols such as
2,2,2-trifluoroethanol (TFE) under acidic conditions. This practical
acid-catalyzed S_N1 reaction opens the door for the synthesis
of novel bifunctional diamondoids. With diamantane as an example, we
show that the resulting monoethers can be used to prepare selectively,
for instance, amino or nitro alcohols and unnatural amino acids. These
are important compounds in terms of the exploration of electronic,
pharmacological, and material properties of functionalized nanodiamonds.

Harvard Citation style: Schwertfeger, H., Würtele, C., Serafin, M., Hausmann, H., Carlson, R., Dahl, J., et al. (2008) Monoprotection of Diols as a Key Step for the Selective Synthesis of Unequally Disubstituted Diamondoids (Nanodiamonds), The Journal of Organic Chemistry, 73(19), pp. 7789-7792. https://doi.org/10.1021/jo801321s

APA Citation style: Schwertfeger, H., Würtele, C., Serafin, M., Hausmann, H., Carlson, R., Dahl, J., & Schreiner, P. (2008). Monoprotection of Diols as a Key Step for the Selective Synthesis of Unequally Disubstituted Diamondoids (Nanodiamonds). The Journal of Organic Chemistry. 73(19), 7789-7792. https://doi.org/10.1021/jo801321s