Synthesis of model long-chain ω-alkenyltrichlorosilanes and triethoxysilanes for the formation of self-assembled monolayers

Tetrahedron

Volumn 62, Issue 4, 2006, Pages 647-651

  Nguyen, Thanh Binh ^a   Castanet, Anne Sophie ^a   Nguyen, Thi Huu ^a   Nguyen, Kim Phi Phung ^a   Bardeau, Jean François ^a   Gibaud, Alain ^a   Mortier, Jacques ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

Functionalized long chain hydrocarbons; Grignard reactions; Silanes

Indexed keywords

CARBON 13; HYDROCARBON; SILANE DERIVATIVE; SILICON; VINYL DERIVATIVE;

ARTICLE; CHEMICAL MODEL; HYDROXYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 28844487489     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.10.003     Document Type: Article

References (46)

1. Reviews: (a) A. Ulman An Introduction to Ultrathin Organic Films: from Langmuir-Blodgett to Self Assembly 1991 Academic Boston, MA
2. A. Ulman Chem. Rev. 96 1996 1533
3. T.P. Sullivan, and W.T.S. Huck Eur. J. Org. Chem. 2003 17
4. J.C. Love, L.A. Estroff, J.K. Kriebel, R.G. Nuzzo, and G.M. Whitesides Chem. Rev. 105 2005 1103
5. Selected publications: (a) R. Maoz, L. Netzer, J. Gun, and J. Sagiv J. Chim. Phys. 85 1988 1059
6. S.W. Keller, H.N. Kim, and T.E. Mallouk J. Am. Chem. Soc. 116 1994 8817
7. K. Ogawa, N. Mino, H. Tamura, and M. Hatada Langmuir 6 1990 851
8. M.E. Thomson Chem. Mater. 6 1994 1168
9. A. Baptiste, A. Gibaud, J.-F. Bardeau, K. Wen, R. Maoz, J. Sagiv, and B.M. Ocko Langmuir 18 2002 3916
10. A. Baptiste, A. Bulou, J.-F. Bardeau, J. Nouet, A. Gibaud, K. Wen, S. Hoeppener, R. Maoz, and J. Sagiv Langmuir 20 2004 6232 and references cited therein
11. G.H. Posner Org. React. (N. Y.) 22 1975 253
12. R. Larock Comprehensive Organic Transformations 1989 VCH New York pp 45-67
13. M. Tamura, and J. Kochi Synthesis 1971 303
14. G. Fouquet, and M. Schlosser Angew. Chem., Int. Ed. Engl. 13 1974 82
15. R.A. Volkmann, J.T. Davis, and C.N. Meltz J. Org. Chem. 48 1983 1767
16. J. Bäckwall, M. Sellen, and B. Grant J. Am. Chem. Soc. 112 1990 6615
17. 4 is an efficient catalyst for cross-coupling of lithiated 1,4-dialkyl-2,5-piperazinedione anions with gramine methosulfate and alkyl halides: (a) J. Gelin, J. Mortier, J. Moyroud, and A. Chêne J. Org. Chem. 58 1993 3473
18. J. Moyroud, J. Gelin, A. Chêne, and J. Mortier Tetrahedron 52 1996 8525
19. Nevertheless, Cu-catalyzed alkylation of secondary and tertiary alkyl Grignards is facilitated by the presence of N-methyl pyrrolidone (4-9 equiv). See: G. Cahiez, C. Chaboche, and M. Jézéquel Tetrahedron 56 2000 2733
20. The soluble copper catalyst 'CuBr-LiBr-LiSPh-THF' is efficient for coupling primary, secondary, tertiary, aryl, vinyl, and allylic Grignard reagents to primary tosylates and primary Grignard reagents to secondary tosylates and mesylates. See: D.H. Burns, J.D. Miller, H.-K. Chan, and M.O. Delaney J. Am. Chem. Soc. 119 1997 2125
21. S.R. Wasserman, Y.-T. Tao, and G.M. Whitesides Langmuir 5 1989 1074
22. N. Balachander, and C.N. Sukenik Langmuir 6 1990 1621
23. F. Effenberger, and S. Heid Synthesis 1995 1126
24. See also: (a) L. Netzer, R. Iscovici, and J. Sagiv Thin Solid films 99 1983 235
25. D.K. Johnson, J.P. Ciavarri, F.T. Ishmael, K.J. Schillinger, T.A.P. Van Geel, and S.M. Stratton Tetrahedron Lett. 36 1995 8565
26. J. Peanaski, H. Schneider, S. Granick, and C. Kessel Langmuir 11 1995 953
27. L. Friedman, and A. Shani J. Am. Chem. Soc. 96 1974 7101
28. Bis-coupling reactions of α,ω-ditosylates with Grignard reagents have been reported: M. Schlosser, and H. Bossert Tetrahedron 47 1991 6287
29. Nard Chemical Ltd (Hyogo) and Matsushita Electric Industrial Co. Ltd (Osaka) supply NTS on demand. To the best of our knowledge, the processes used are neither patented nor published.
30. Octane-1,8-diol is commercial. For the preparation of tetradecane-1,14-diol, see: M. Rodriguez, M. Llinares, S. Doulut, A. Heitz, and J. Martinez Tetrahedron Lett. 32 1991 923
31. S. Chatti, M. Bortolussi, and A. Loupy Tetrahedron 56 2000 5877
32. Organomagnesiums couple efficiently with ω-chloroalkyl-p-toluene sulfonates: see Ref. 10. Reactions of Grignard reagents with alkylsulfonates: (a) K. Mori, and H. Takikawa Tetrahedron 46 1990 3139
33. Y. Shirai, M. Seki, and K. Mori Eur. J. Org. Chem. 1999 3139
34. Y. Nakamura, and K. Mori Eur. J. Org. Chem. 2000 1307
35. B.H. Lipshutz Org. React. (N. Y.) 41 1992 135
36. B.H. Lipshutz Synlett 1990 119
37. B.H. Lipshutz, R.S. Wilhelm, and J.A. Kozlowski Tetrahedron 40 1984 5005
38. J. Kochi Organometallic Mechanisms and Catalysts 1978 Academic New York p 381
39. M. Schlosser Angew. Chem., Int. Ed. Engl. 13 1974 701
40. The term 'higher-order' cuprates is meant to imply only a stoichiometric relationship within the cuprate.
41. C.C. Tseng, S.D. Paisley, and H.L. Goering J. Org. Chem. 51 1986 2884
42. J. Mortier, M. Vaultier, R. Cantegril, and P. Dellis Aldrichim. Acta 30 1997 34
43. F. Gohier, and J. Mortier J. Org. Chem. 68 2003 2030
44. See also: (c) T.H. Nguyen, N.T. Chau, A.-S. Castanet, K.P.P. Nguyen, and J. Mortier Org. Lett. 7 2005 2445
45. Under similar conditions, commercial 11-bromoundec-1-ene gave triethoxy(undec-10-enyl)silane in 65% yield.
46. M. Schlosser Organometallics in Synthesis. A Manual 2nd ed. 2002 Wiley Chichester