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Monoprotection of diols as a key step for the selective synthesis of unequally disubstituted diamondoids (nanodiamonds).

Authors :
Schwertfeger H
Würtele C
Serafin M
Hausmann H
Carlson RM
Dahl JE
Schreiner PR
Source :
The Journal of organic chemistry [J Org Chem] 2008 Oct 03; Vol. 73 (19), pp. 7789-92. Date of Electronic Publication: 2008 Aug 29.
Publication Year :
2008

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(N)1 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.

Details

Language :
English
ISSN :
1520-6904
Volume :
73
Issue :
19
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
18761438
Full Text :
https://doi.org/10.1021/jo801321s