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Synthesis 2012(2): 259-264  
DOI: 10.1055/s-0031-1289617
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Diamondoid Carboxylic Acids

Natalie A. Fokinaa, Boryslav A. Tkachenkoa, Jeremy E. P. Dahlb, Robert M. K. Carlsonb, Andrey A. Fokin*a,c, Peter R. Schreiner*a
a Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany
Fax: +49(641)9934309; e-Mail: prs@org.chemie.uni-giessen.de;
b Stanford University, Stanford Institute for Materials & Energy Science, 476 Lomita Mall, Stanford, CA 94305, USA
c Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine
e-Mail: aaf@xtf.ntu-kpi.kiev.ua;
Further Information

Publication History

Received 21 October 2011
Publication Date:
23 November 2011 (online)

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Abstract

Procedures for the synthesis of apical mono-, di-, and tricarboxylic acids of triamantane, [121]tetramantane, and [1(2,3)4]pentamantane, apical diacetic acids of diamantane and triamantane, as well as medial propionic acids of diamantane and triamantane were elaborated starting from the corresponding alcohols and bromides. The obtained diamondoid acids were characterized as their methyl ester derivatives.

Key words

bromides - carboxylic acids - diamondoids - esters - hydrocarbons - nanostructures

    References

  • 1 Schwertfeger H. Fokin AA. Schreiner PR. Angew. Chem. Int. Ed.  2008,  47:  1022 
    Google Scholar
  • 2 Balaban AT. Schleyer P. v. R. Tetrahedron  1978,  34:  3599 
    Google Scholar
  • 3 Dahl JEP. Moldowan JM. Peakman TM. Clardy JC. Lobkovsky E. Olmstead MM. May PW. Davis TJ. Steeds JW. Peters KE. Pepper A. Ekuan A. Carlson RMK. Angew. Chem. Int. Ed.  2003,  42:  2040 
    Google Scholar
  • 4a Kesters E. Claes M. Le QT. Lux M. Franquet A. Vereecke G. Mertens PW. Frank MM. Carleer R. Adriaensens P. Biebuyk JJ. Bebelman S. Thin Solid Films  2008,  516:  3454 
    Google Scholar
  • 4b Matsukawa D. Okamura H. Shirai M. J. Mater. Chem.  2011,  21:  10407 
    Google Scholar
  • 4c Böhm I. Isenbügel K. Ritter H. Branscheid R. Kolb U. Angew. Chem. Int. Ed.  2011,  50:  7896 
    Google Scholar
  • 4d Morcombea CR. Zilm KW. J. Magn. Reson.  2003,  162:  479 
    Google Scholar
  • 5a Maugh T. Science  1979,  206:  1058 
    Google Scholar
  • 5b Govorkova EA. Fang HB. Tan M. Webster RG. Antimicrob. Agents Chemother.  2004,  48:  4855 
    Google Scholar
  • 5c Rosenthal KS. Sokol MS. Ingram RL. Subramanian R. Fort RC. Antimicrob. Agents Chemother.  1982,  22:  1031 
    Google Scholar
  • 6 Dahl JE. Liu SG. Carlson RMK. Science  2003,  299:  96 
    Google Scholar
  • 7a Sinkel C. Agarwal S. Fokina NA. Schreiner PR. J. Appl. Polym. Sci.  2009,  114:  2109 
    Google Scholar
  • 7b Ishizone T. Tajima H. Torimae H. Nakahama S. Macromol. Chem. Phys.  2002,  203:  2375 
    Google Scholar
  • 8 Schreiner PR. Fokina NA. Tkachenko BA. Hausmann H. Serafin M. Dahl JEP. Liu S. Carlson RMK. Fokin AA. J. Org. Chem.  2006,  71:  6709 
    Google Scholar
  • 9 Fokina NA. Tkachenko BA. Merz A. Serafin M. Dahl JEP. Carlson RMK. Fokin AA. Schreiner PR. Eur. J. Org. Chem.  2007,  4738 
    Google Scholar
  • 10 Fokin AA. Gunchenko PA. Novikovsky AA. Shubina TE. Chernyaev BV. Dahl JEP. Carlson RMK. Yurchenko AG. Schreiner PR. Eur. J. Org. Chem.  2009,  5153 
    Google Scholar
  • 11 Fokin AA. Butova ED. Chernish LV. Fokina NA. Dahl JEP. Carlson RMK. Schreiner PR. Org. Lett.  2007,  9:  2541 
    Google Scholar
  • 12 Willey TM. Fabbri JD. Lee JRI. Schreiner PR. Fokin AA. Tkachenko BA. Fokina NA. Dahl JEP. Carlson RMK. Vance AL. Yang W. Terminello LJ. van Buuren T. Melosh NA. J. Am. Chem. Soc.  2008,  130:  10536 
    Google Scholar
  • 13a Yang WL. Fabbri JD. Willey TM. Lee JRI. Dahl JE. Carlson RMK. Schreiner PR. Fokin AA. Tkachenko BA. Fokina NA. Meevasana W. Mannella N. Tanaka K. Zhou XJ. van Buuren T. Kelly MA. Hussain Z. Melosh NA. Shen Z.-X. Science  2007,  316:  1460 
    Google Scholar
  • 13b Clay WA. Liu Z. Yang W. Fabbri JD. Dahl JE. Carlson RMK. Sun Y. Schreiner PR. Fokin AA. Tkachenko BA. Fokina NA. Pianetta PA. Melosh N. Shen Z.-X. Nano Lett.  2009,  9:  57 
    Google Scholar
  • 13c Roth S. Leuenberger D. Osterwalder J. Dahl JE. Carlson RMK. Tkachenko BA. Fokin AA. Schreiner PR. Hengsberger M. Chem. Phys. Lett.  2010,  495:  102 
    Google Scholar
  • 14 Drummond ND. Williamson AJ. Needs RJ. Galli G. Phys. Rev. Lett.  2005,  95:  096801 
    Google Scholar
  • 15a Lysenko AB. Senchyk GA. Lincke J. Lassig D. Fokin AA. Butova ED. Schreiner PR. Krautscheid H. Domasevitch KV. Dalton Trans.  2010,  4223 
    Google Scholar
  • 15b Ren C. Zhang Y.-N. Shi W.-J. Liu B. Wang Y.-Y. Shi Q.-Z. CrystEngComm  2011,  13:  5179 
    Google Scholar
  • 16 Hollowood F. Karim A. McKervey MA. McSweeney P. Duddeck H. J. Chem. Soc., Chem. Commun.  1978,  306 
    Google Scholar
  • 17 Bott K. Hellmann H. Angew. Chem., Int. Ed. Engl.  1966,  5:  870 
    Google Scholar
  • 18 Ohno M. Ishizaki K. Eguchi S. J. Org. Chem.  1988,  53:  1285 
    Google Scholar
  • 19 Fokin AA. Tkachenko BA. Gunchenko PA. Gusev DV. Schreiner PR. Chem. Eur. J.  2005,  11:  7091 
    Google Scholar
  • 20 Miller LL. Koch VR. Koenig T. Tuttle M. J. Am. Chem. Soc.  1973,  95:  5075 
    Google Scholar
  • 21 Fokin AA. Schreiner PR. Fokina NA. Tkachenko BA. Hausmann H. Serafin M. Dahl JEP. Liu S. Carlson RMK. J. Org. Chem.  2006,  71:  8532 
    Google Scholar
  • 22 Courtney T. Johnston DE. Rooney JJ. McKervey MA. J. Chem. Soc., Perkin Trans. 1  1972,  2691 
    Google Scholar