Versatile and efficient synthesis of ω-functionalized asymmetric disulfides via sulfenyl bromide adducts

Langmuir

Volumn 23, Issue 5, 2007, Pages 2318-2321

  Kowalczyk, Janusz ^a   Barski, Piotr ^a   Witt, Dariusz ^b   Grzybowski, Bartosz A ^c  

^a ProChimia Surfaces   (Poland)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^c Northwestern University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDUCTS; DISULFIDES; HALIDES; SULFENYL BROMIDE;

ACIDITY; ALKALINITY; AROMATIC COMPOUNDS; HALOGEN COMPOUNDS; SELF ASSEMBLED MONOLAYERS; SYNTHESIS (CHEMICAL);

SULFUR COMPOUNDS;

BROMIDE; DISULFIDE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; METHODOLOGY; PHYSICAL CHEMISTRY;

BROMIDES; CATALYSIS; CHEMISTRY, PHYSICAL; DISULFIDES; ELECTROCHEMISTRY; MODELS, CHEMICAL; MOLECULAR STRUCTURE;

EID: 33847761523     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la063013k     Document Type: Article

References (41)

1. Witt, D.; Klajn, R.; Barski, P.; Grzybowski, B. A. Curr. Org. Chem. 2004, 8, 1763-1797.
2. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103-1069.
3. Ulman, A. Chem. Rev. 1996, 96, 1533-1554.
4. Houseman, B. T.; Gawalt, E. S.; Mrksich, M. Langmuir 2003, 19, 1522-1531.
5. Chen, S. F.; Li, L. Y.; Boozer, C. L.; Jiang, S. Y. J. Phys. Chem. B 2001, 105, 2975-2980.
6. Shon, Y. S.; Mazzitelli, C.; Murray, R. W. Langmuir 2001, 17, 7735-7741.
7. Higashi, N.; Takahashi, M.; Niwa, M. Langmuir 1999, 15, 111-115.
8. O'Brien, J. C.; Stickney, J. T.; Porter, M. D. Langmuir 2000, 16, 9559-9567.
9. (a) Kalsin, A. K.; Fialkowski, M.; Paszewski, M.; Smoukov, S. K.; Bishop, K. J. M.; Grzybowski, B. A. Science 2006, 312, 420-424.
10. (b) Kalsin, A. K.; Smoukov, S. K.; Kowalczyk, B.; Klajn, R.; Grzybowski, B. A. J. Am. Chem. Soc. 2006, 128, 15046-15047.
11. Modena, G.; Capozzi, G. The Chemistry of the Thiol Group; Patai, S. Ed.: Wiley: New York, 1974; Part 2, Chapter 17.
12. (a) Yoneda, F.; Suzuki, K.; Nitta, Y. J. Am. Chem. Soc. 1966, 88, 2328-2329.
13. Yoneda, F.; Suzuki, K.; Nitta, Y. J. Org. Chem. 1967, 32, 727-729.
14. (b) Mukaiyama, T.; Takahashi, K. Tetrahedron Lett. 1968, 9, 5907-5908.
15. (c) Kato, K.; Mitsunobu, O. J. Org. Chem. 1970, 35, 4227-4229.
16. (d) Boekelheide, V.; Mondt, J. L. Tetrahedron Lett. 1970, 11, 1203-1206.
17. (e) Endo, T.; Tasai, H.; Ishigami, T. Chem. Lett. 1975, 813-815.
18. (f) Vedejs, E.; Arnost, M. J.; Hagen, J. P. J. Org. Chem. 1979, 44, 3230-3238.
19. Suzuki, H.; Kawato, S.; Nasu, A. Bull. Chem. Soc. Jpn. 1992, 65, 626-627.
20. a) Vida, J. A. Tetrahedron Lett. 1970, 11, 3447-3448.
21. (b) Harpp, D. N.; Ash, D. K.; Back, T. G.; Gleason, J. G.; Orwing, B. A.; Vanhorn, W. F.; Snyder, J. P. Tetrahedron Lett. 1970, 11, 3551-3554.
22. Alonso, M. E.; Aragono, H. In Organic Syntheses; Wiley: New York, 1988; Collect. Vol 4, pp 235-241.
23. Harpp, D. N.; Friedlander, B. T.; Larsne, C. J. Org. Chem. 1978, 43, 3481-3485.
24. (a) Ledung, G.; Bergkvist, M.; Quist, A. P.; Gelius, U.; Carlsson, J.; Oscarsson, S. Langmuir 2001, 17, 6056-6058.
25. (b) McAllan, D. T.; Cullum, T. V.; Dean, R. A.; Fidler, F. A. J. Am. Chem. Soc. 1951, 73, 3627-3632.
26. Jayasuriya, N.; Regen, S. L. Tetrahedron Lett. 1992, 33, 451-452.
27. Masui, M.; Mizuki, Y.; Sakai, K.; Ueda, C.; Ohmori, H. J. Chem. Soc., Chem. Commun. 1984, 843-844.
28. Schroll, A. L.; Barany, G. J. Org. Chem. 1989, 54, 244-247.
29. (a) Almasi, L.; Hants, A. Chem. Ber. 1970, 103, 718-721.
30. (b) Lopusinski, A.; Potrzebowski, M. Phosphorus Sulfur Relat. Elem. 1987, 32, 55-64.
31. (c) Shi, M.; Kato, S. Helv. Chim. Acta 2002, 85, 2559-2563.
32. Edmundson, R. S. Tetrahedron 1965, 21, 2379-2387.
33. Kandere-Grzybowska, K.; Campbell, C. J.; Komarova, Y.; Grzybowski, B. A.; Borisy, G. G. Nat. Methods 2005, 2, 739-741.
34. Wilson, S. D.; Nock, S. Angew. Chem., Int. Ed. 2003, 42, 494-500.
35. Sigal, G. B.; Bamdad, C.; Barberis, A.; Strominger, J.; Whitesides, G. M. Anal. Chem. 1996, 68, 490-497.
36. Chen, C. S. Personal communication.
37. Houseman, B. T.; Gawalt, E. S.; Mrksich, M. Langmuir 2003, 19, 1522-1531.
38. Grosa, G.; Viola, F.; Ceruti, M.; Brusa, P.; Delprino, L. Eur. J. Med. Chem. Chim. Ther. 1994, 29, 17-24.
39. Lee, S.; Anzai, J.; Osa, T. Bull. Chem. Soc. Jpn. 1991, 64, 2019-2021.
40. Hodneland, C. D.; Lee, Y.-S.; Min, D.-H.; Mrksich, M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5048-5052.
41. Hodneland, C. D.; Campbell, S.; Duffy, D.; Agosto, M.; Wang, E. Surface Logix, Inc., U.S.A.; PCT Int. Appl., 2003.