Synthesis of Diamondoid Carboxylic
Acids

Natalie A. Fokina; Boryslav A. Tkachenko; Jeremy E. P. Dahl; Robert M. K. Carlson; Andrey A. Fokin; Peter R. Schreiner

doi:10.1055/s-0031-1289617

PAPER

Synthesis of Diamondoid Carboxylic Acids

Natalie A. Fokina^a, Boryslav A. Tkachenko^a, Jeremy E. P. Dahl^b, Robert M. K. Carlson^b, 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;

Abstract

All articles of this category

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

Full Text

References

<A NAME="RZ99311SS-1">1</A> Schwertfeger H. Fokin AA. Schreiner PR. Angew. Chem. Int. Ed. 2008, 47: 1022

<A NAME="RZ99311SS-2">2</A> Balaban AT. Schleyer P. v. R. Tetrahedron 1978, 34: 3599

<A NAME="RZ99311SS-3">3</A> 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

<A NAME="RZ99311SS-4A">4a</A> 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

<A NAME="RZ99311SS-4B">4b</A> Matsukawa D. Okamura H. Shirai M. J. Mater. Chem. 2011, 21: 10407

<A NAME="RZ99311SS-4C">4c</A> Böhm I. Isenbügel K. Ritter H. Branscheid R. Kolb U. Angew. Chem. Int. Ed. 2011, 50: 7896

<A NAME="RZ99311SS-4D">4d</A> Morcombea CR. Zilm KW. J. Magn. Reson. 2003, 162: 479

<A NAME="RZ99311SS-5A">5a</A> Maugh T. Science 1979, 206: 1058

<A NAME="RZ99311SS-5B">5b</A> Govorkova EA. Fang HB. Tan M. Webster RG. Antimicrob. Agents Chemother. 2004, 48: 4855

<A NAME="RZ99311SS-5C">5c</A> Rosenthal KS. Sokol MS. Ingram RL. Subramanian R. Fort RC. Antimicrob. Agents Chemother. 1982, 22: 1031

<A NAME="RZ99311SS-6">6</A> Dahl JE. Liu SG. Carlson RMK. Science 2003, 299: 96

<A NAME="RZ99311SS-7A">7a</A> Sinkel C. Agarwal S. Fokina NA. Schreiner PR. J. Appl. Polym. Sci. 2009, 114: 2109

<A NAME="RZ99311SS-7B">7b</A> Ishizone T. Tajima H. Torimae H. Nakahama S. Macromol. Chem. Phys. 2002, 203: 2375

<A NAME="RZ99311SS-8">8</A> Schreiner PR. Fokina NA. Tkachenko BA. Hausmann H. Serafin M. Dahl JEP. Liu S. Carlson RMK. Fokin AA. J. Org. Chem. 2006, 71: 6709

<A NAME="RZ99311SS-9">9</A> Fokina NA. Tkachenko BA. Merz A. Serafin M. Dahl JEP. Carlson RMK. Fokin AA. Schreiner PR. Eur. J. Org. Chem. 2007, 4738

<A NAME="RZ99311SS-10">10</A> Fokin AA. Gunchenko PA. Novikovsky AA. Shubina TE. Chernyaev BV. Dahl JEP. Carlson RMK. Yurchenko AG. Schreiner PR. Eur. J. Org. Chem. 2009, 5153

<A NAME="RZ99311SS-11">11</A> Fokin AA. Butova ED. Chernish LV. Fokina NA. Dahl JEP. Carlson RMK. Schreiner PR. Org. Lett. 2007, 9: 2541

<A NAME="RZ99311SS-12">12</A> 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

<A NAME="RZ99311SS-13A">13a</A> 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

<A NAME="RZ99311SS-13B">13b</A> 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

<A NAME="RZ99311SS-13C">13c</A> Roth S. Leuenberger D. Osterwalder J. Dahl JE. Carlson RMK. Tkachenko BA. Fokin AA. Schreiner PR. Hengsberger M. Chem. Phys. Lett. 2010, 495: 102

<A NAME="RZ99311SS-14">14</A> Drummond ND. Williamson AJ. Needs RJ. Galli G. Phys. Rev. Lett. 2005, 95: 096801

<A NAME="RZ99311SS-15A">15a</A> Lysenko AB. Senchyk GA. Lincke J. Lassig D. Fokin AA. Butova ED. Schreiner PR. Krautscheid H. Domasevitch KV. Dalton Trans. 2010, 4223

<A NAME="RZ99311SS-15B">15b</A> Ren C. Zhang Y.-N. Shi W.-J. Liu B. Wang Y.-Y. Shi Q.-Z. CrystEngComm 2011, 13: 5179

<A NAME="RZ99311SS-16">16</A> Hollowood F. Karim A. McKervey MA. McSweeney P. Duddeck H. J. Chem. Soc., Chem. Commun. 1978, 306

<A NAME="RZ99311SS-17">17</A> Bott K. Hellmann H. Angew. Chem., Int. Ed. Engl. 1966, 5: 870

<A NAME="RZ99311SS-18">18</A> Ohno M. Ishizaki K. Eguchi S. J. Org. Chem. 1988, 53: 1285

<A NAME="RZ99311SS-19">19</A> Fokin AA. Tkachenko BA. Gunchenko PA. Gusev DV. Schreiner PR. Chem. Eur. J. 2005, 11: 7091

<A NAME="RZ99311SS-20">20</A> Miller LL. Koch VR. Koenig T. Tuttle M. J. Am. Chem. Soc. 1973, 95: 5075

<A NAME="RZ99311SS-21">21</A> Fokin AA. Schreiner PR. Fokina NA. Tkachenko BA. Hausmann H. Serafin M. Dahl JEP. Liu S. Carlson RMK. J. Org. Chem. 2006, 71: 8532

<A NAME="RZ99311SS-22">22</A> Courtney T. Johnston DE. Rooney JJ. McKervey MA. J. Chem. Soc., Perkin Trans. 1 1972, 2691

Supplementary Material

Supporting Information