The preparation of three new partially deuterated hexadecanethiols for applications in surface chemistry

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 51, Issue 12, 2008, Pages 391-398

  Sheepwash, Erin E ^a   Rowntree, Paul A ^a   Schwan, Adrian L ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Deuterium; Grignard reaction; Self assembled monolayers; Thiol

Indexed keywords

ADDITION REACTIONS; DIMERIZATION; GOLD NANOPARTICLES; SELF ASSEMBLED MONOLAYERS; SURFACE CHEMISTRY;

ATOM MIGRATION; AU NANOPARTICLE; AU(1 1 1 ); COUPLING CHEMISTRY; GRIGNARD COUPLING; GRIGNARD REACTION; HEXADECANE THIOLS; MECHANISTICS; RING OPENING; THIOL;

DEUTERIUM;

ACETIC ACID; DEUTERIUM; GOLD; GOLD 111; HEXADECANE; HEXADECANETHIOL DERIVATIVE; NANOPARTICLE; SULFUR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; DIMERIZATION; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

EID: 55049093010     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1541     Document Type: Article

References (31)

1. A. Ulman, Chem. Rev. 1996, 96, 1533-1554.
2. A. D. Buckingham, H. G. E. Hentschel, J. Polym. Sci., Polym. Phys. Ed. 1980, 18, 853-861.
3. E. Garand, P. A. Rowntree, J. Phys. Chem. B 2005, 109, 12927-12934.
4. E. Garand, J.-F. Picard, P. Rowntree, J. Phys. Chem. B 2004, 108, 8182-8189.
5. M. A. Huels, P.-C. Dugal, L. Sanche, J. Chem. Phys. 2003, 118, 11168-11178.
6. R. A. MacPhail, H. L. Strauss, R. G. Snyder, C. A. Elliger, J. Phys. Chem. 1984, 88, 334-341.
7. A. N. Parikh, D. L. Allara, J. Chem. Phys. 1992, 96, 927-945.
8. A. P. Tulloch, Prog. Lipid. Res. 1983, 22, 235-256.
9. A. Badia, L. Demers, L. Dickinson, F. G., Morin, R. B. Lennox, L. Reven, J. Am. Chem. Soc. 1997, 119, 11104-11105.
10. M. Tamura, J. Kochi, Synthesis 1971, 303-305.
11. D. K. Johnson, J. Donahoe, J. Kang, Synth. Commun. 1994, 24, 1557-1564.
12. N. Balachander, C. N. Sukenik, Langmuir 1990, 6, 1621-1627.
13. I. Jablonkai, P. Oroszlan, Chem. Phys. Lipids 2005, 133, 103-112.
14. T. D. Clark, E. C. Dugan, Synthesis 2006, 1083-1086.
15. S. Maisch, F. Buckel, F. Effenberger, J. Am. Chem. Soc. 2005, 127, 17315-17322.
16. D. Qin, H.-S. Byun, R. Bittman, J. Org. Chem. 1996, 61, 8709-8711.
17. A. Dion, P. Dube, C. Spino, Org. Lett. 2005, 7, 5601-5604. We thank Prof. Spino for sharing additional experimental details about this chemistry.
18. L. H. Long, G. F. Freeguard, Nature 1965, 207, 403.
19. A. T. Khan, E. Mondal, Synlett 2003, 694-698.
20. H. A. Bates, J. Farina, M. Tong, J. Org. Chem. 1986, 51, 2637-2641.
21. R. P. Volante, Tetrahedron Lett. 1981, 22, 3119-3122.
22. X. Qin, T. Tzvetkov, X. Liu, D.-C. Lee, L. Yu, D. C. Jacobs, J. Am. Chem. Soc. 2004, 126, 13232-13233.
23. J. Christoffers, H. Oertling, Tetrahedron 2000, 56, 1339-1344.
24. K. Sasaki, K. Sugou, K. Miyamoto, J.-i. Hirai, S. Tsubouchi, H. Miyasaka, A. Itaya, Y. Kuroda, Org. Biomol. Chem. 2004, 2, 2852-2860.
25. H. Takikawa, H. Tamagawa, K. Mori, J. Indian Chem. Soc. 1997, 74, 855-857.
26. Z. You, M. Koreeda, Tetrahedron Lett. 1993, 34, 2597-2600.
27. K. S. S. Akasaka, S. Matsuoka, M. Murata, H. Meguro, Biosci. Biotechnol. Biochem. 2000, 64, 1842-1846.
28. 3MgI was not directly coupled to compound 23 due to separation issues between 23 and the starting 1,12-dibromododecane.
29. R. J. Faragher, D. Alberico, A. L. Schwan, Tetrahedron 2005, 61, 1115-1125.
30. K. F. Bernady, M. B. Floyd, J. F. Poletto, M. J. Weiss, J. Org. Chem. 1979, 44, 1438-1447.
31. A. N. Rai, A. Basu, Org. Lett. 2004, 6, 2861-2863.