10772
C. Wiles et al. / Tetrahedron 61 (2005) 10757–10773
9. Wiles, C.; Watts, P.; Haswell, S. J.; Pombo-Villar, E. Lab Chip
2001, 1, 100–101.
36. Howard, A. S.; Meerholz, C. A.; Michael, J. P. Tetrahedron
Lett. 1979, 15, 1339–1340.
10. Wiles, C.; Watts, P.; Haswell, S. J.; Pombo-Villar, E.
Tetrahedron 2004, 60, 8421–8427.
37. House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org.
Chem. 1969, 34, 2324–2336.
11. Wiles, C.; Watts, P.; Haswell, S. J.; Pombo-Villar, E. Lab Chip
2004, 4, 171–173.
38. Veysoglu, T.; Mitscher, L. A. Tetrahedron Lett. 1981, 22,
1299–1302.
¨
12. Ehrfeld, W.; Hessel, V.; Lowe, H. Microreactors: New
Technology for Modern Chemistry; Wiley-VCH: New York,
2000.
39. Morita, T.; Okamoto, Y.; Sakurai, H. Tetrahedron Lett. 1980,
21, 835–838.
40. Kita, Y.; Haruta, J.; Segawa, J.; Tamura, Y. Tetrahedron Lett.
1979, 20, 4311–4314.
13. McCreedy, T. Anal. Chim. Acta 2001, 427, 39–43.
14. (a) Reyes, D. R.; Iossifidis, D.; Auroux, P. A.; Manz, A. Anal.
Chem. 2002, 74, 2626–2636. (b) Reyes, D. R.; Iossifidis, D.;
Auroux, P. A.; Manz, A. Anal. Chem. 2002, 74, 2637–2652.
(c) Woias, P. In Microfluidics and BioMEMS, Mastrangelo,
C. H.; Becker, H., Eds. SPIE Conference Proceedings 2001,
2001, 4560, 39.
41. Nakamra, E.; Murofushi, T.; Shimizu, M.; Kuwajima, I. J. Am.
Chem. Soc. 1976, 98, 2346–2348.
42. LeBel, N. A.; Cherluck, R. M.; Curtius, E. A. Synthesis 1973,
678–679.
43. Cooke, M. P., Jr.; Pollock, C. M. J. Org. Chem. 1993, 58,
7474–7481.
15. Manz, A.; Fettinger, J. C.; Ludi, H.; Widmer, H. M.; Harrison,
J. D. Trends Anal. Chem. 1991, 10, 144–149.
44. Picquet, M.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1999,
55, 3937–3948.
16. Dasgupta, P. K.; Lui, S. Anal. Chem. 1994, 66, 1792–1798.
17. Seller, K.; Fan, Z. H.; Fluri, K.; Harrison, D. J. Anal. Chem.
1994, 66, 3485–3491.
45. Oediger, H.; Moller, F.; Eiter, K. Synthesis 1972, 591–598.
46. Flynn, K. G.; Nenortas, D. R. J. Org. Chem. 1963, 28,
3527–3530.
18. Manz, A.; Effenhauser, C. S.; Buggraf, N.; Harrison, J. D.;
Seiler, K.; Fluri, K. J. Micromech. Microeng. 1994, 4, 257.
19. Boer, G.; Dodge, A.; Fluri, K.; van der Schoot, H.; Verpoorte,
E.; de Rooji, N. F. In Micro Total Analysis Systems; Ramsey,
J. M., van den Berg, A., Eds.; Kluwer: Dordecht, 1998;
pp 53–56.
47. Barton, D. H. R.; Elliot, J. D.; Gero, S. D. J. Chem. Soc.,
Perkin Trans. 1 1982, 2085–2090.
48. Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.;
Schmidt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435–2454.
49. Schwesinger, R.; Schlemper, H.; Hasenfratz, C.; Willaredt, J.;
Dambacher, T.; Breuer, T.; Ottaway, C.; Fletschinger, M.;
Boele, J.; Fritz, H.; Putzas, D.; Roter, H. W.; Bordwell, F. G.;
Satish, A. V.; Ji, J.; Peters, E.; Peters, K.; von Schnering, H. G.;
Walz, L. Liebigs Ann. Chem. 1996, 1055–1081.
50. Schwesinger, R.; Hasenfratz, C.; Schlemper, H.; Walz, E.;
Peters, E.; Peters, K.; von Schnering, H. G. Angew. Chem., Int.
Ed. Engl. 1993, 32, 1361–1363.
20. Christensen, P. D.; Johnson, S. W. P.; McCreedy, T.; Skelton,
V.; Wilson, N. G. Anal. Commun. 1998, 35, 341–342.
21. Zeng, S.; Chen, C.; Mikkelsen, J. C., Jr.; Santiago, J. G. Sens.
Actuators, B 2001, 79, 107–114.
22. Fletcher, P. D. I.; Haswell, S. J.; Zhang, X. Lab Chip 2002, 2,
102–112.
23. Rice, C. L.; Whitehead, R. J. Phys. Chem. 1965, 69,
4017–4024.
51. Schwesinger, R. Angew. Chem., Int. Ed. Engl. 1987, 26,
1164–1167.
24. Haswell, S. J.; Middleton, R. J.; O’Sullivan, B.; Skelton, V.;
Watts, P.; Styring, P. J. Chem. Soc., Chem. Commun. 2001,
391–398.
52. In addition, we investigated the manipulation of a stronger
phosphazene derivative, P4-t-Bu 46 (0.25 M in anhydrous
THF), by EOF. Application of 417 V cmK1, resulted in the
successful mobilisation of the reagent at a flow rate of
0.15 ml minK1. Analysis of the product reservoir by TLC
confirmed the successful transfer of P4-t-Bu 46 from reservoir
B–D.
25. Snyder, L. R. J. Chromatogr. A 1974, 92, 223–230.
26. Smits, J. G. Sens. Actuators, A 1990, 21, 203–206.
27. Makino, E.; Mitsuya, T.; Shibata, T. Sens. Actuators, A 2001,
88, 256–262.
28. Shoji, S.; Nakagakawa, S.; Esashi, M. Sens. Actuators, B 1990,
21, 189–192.
53. O’Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc.
1996, 118, 6070–6071.
29. (a) Bings, N. H.; Wang, C.; Skinner, C. D.; Colyer, C. L.;
Thibault, P.; Harrison, D. J. Anal. Chem. 1999, 71, 3292–3926.
(b) Nittis, V.; Fortt, R.; Legge, C. H.; de Mello, A. J. Lab Chip
2001, 1, 148–152.(c) Gray, B. L.; Collins, S. D.; Smith, R. L.
In Micro total analysis systems, Ramsey, J. M., van den Berg,
A., Eds. Kluwer: Enschede, 2001; Vol. 1, pp 153–158.
30. Kikuntani, Y.; Hibara, A.; Uchiyama, K.; Hisamoto, H.;
Tokeshi, M.; Kitamori, T. Lab Chip 2002, 2, 193–196.
31. House, H.; Auerbach, R. A.; Gall, M.; Peet, P. J. Org. Chem.
1972, 38, 514–522.
54. (a) Skelton, V. An Investigation of Synthetic and Combinator-
ial Reactions in Miniaturised Devices. PhD Thesis, The
University of Hull, 2000, 114. (b) Skelton, V.; Greenway,
G. M.; Haswell, S. J.; Styring, P.; Morgan, D. O.; Warrington,
B. H.; Wong, S. Y. F. Analyst 2001, 126, 7–10. (c) Skelton, V.;
Greenway, G. M.; Haswell, S. J.; Styring, P.; Morgan, D. O.;
Warrington, B. H.; Wong, S. Y. F. Analyst 2001, 126, 11–13.
55. Pederson, C. J. J. Am. Chem. Soc. 1967, 89, 7017–7036.
56. Alternatively micro-scale reactions could be performed in an
inert atmosphere, i.e. glove-box purged with N2.
57. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981,
103, 2127–2129.
32. Deitch, J.; Rathke, M. W. Tetrahedron Lett. 1971, 12,
2953–2956.
33. Rathke, M. W.; Tirpak, R. E. J. Org. Chem. 1982, 47,
5099–5102.
58. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc.
1982, 104, 1737–1739.
¨
59. Ehrfeld, W.; Hessel, V.; Lowe, H. Microreactors: New
Technology for Modern Chemistry; Wiley-VCH: New York,
2000.
34. (a) Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18,
181–187. (b) Kuwajima, I.; Nakamura, E.; Hashimoto, K. Org.
Synth. 1982, 61, 122–128.
35. Noyori, R.; Yokoyma, K.; Sakata, J.; Kuwajima, I.; Nakamura,
E.; Shimizu, M. J. Am. Chem. Soc. 1977, 97, 1265–1266.
60. Suga, S.; Okajima, M.; Fujiwara, K.; Yoshida, J. J. Am. Chem.
Soc. 2001, 123, 7941–7942.