Mild and reliable cleavage sequence for phenoxy acetates

Tetrahedron Letters

Volumn 45, Issue 42, 2004, Pages 7911-7914

  Mirk, Daniela ^a   Waldvogel, Siegfried R ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Azide; Cleavage; Curtius rearrangement; Deprotection; Phenoxy acetates; Protecting groups

Indexed keywords

ACETIC ACID DERIVATIVE; PHENOL DERIVATIVE;

ARTICLE; CURTIUS REARRANGEMENT; REACTION ANALYSIS; SAPONIFICATION;

EID: 4644328148     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.147     Document Type: Article

References (34)

1. B. Kramer, R. Fröhlich, K. Bergander, and S.R. Waldvogel Synthesis 2003 91 96
2. D. Mirk, A. Willner, R. Fröhlich, and S.R. Waldvogel Adv. Synth. Catal. 346 2004 675 681
3. D. Mirk, O. Kataeva, R. Fröhlich, and S.R. Waldvogel Synthesis 2003 2410 2414
4. P.J. Kocieński Protecting Groups 3rd ed. 2004 Georg Thieme Stuttgart
5. T.W. Green, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 John Wiley & Sons New York
6. H. Sobotka, and J. Austin J. Am. Chem. Soc. 74 1952 3813 3815
7. A.M. Bernard, M.R. Ghiani, P.P. Piras, and A. Rivoldini Synthesis 1989 287 289
8. O. Kruber, and A. Schmitt Chem. Ber. 64 1931 2270 2277
9. G. Chuchani, R.M. Doinguez, A. Rotinov, and I. Martin J. Phys. Org. Chem. 12 1999 612 618
10. D. Deffieux, I. Fabre, C. Courseille, and S. Quideau J. Org. Chem. 67 2002 4458 4465
11. J. Peller, O. Wiest, and P.V. Kamat J. Phys. Chem. 105 2001 3176 3181
12. C.S. Rajesh, T.L. Thanulingam, and S. Das Tetrahedron 53 1997 16817 16834
13. P. Boule, A. Zeral, and T. Sehili Z. Phys. Chem. (Munich) 213 1999 87 92
14. W.G. Christiansen J. Am. Chem. Soc. 48 1926 460 468
15. A.J. Birch J. Chem. Soc. 1947 102 104
16. Compound 1a: J. Belleney, J. Vebrel, and E. Cerutti J. Heterocycl. Chem. 21 1984 1431 1435
17. Compound 1b: T. Ahvonen, G. Brunow, P. Kristersson, and K. Lundquist Acta Chem. Scand. Ser. B 37 1983 845 850
18. Compound 1c: see Ref. 1
19. Compound 1d: V. Baliah, and R. Gurumurthy Indian J. Chem. Sect. B 20 1981 629 631
20. Compound 1e: S.P. Green, and D.A. Whiting J. Chem. Soc. Perkin Trans. 1 1998 193 202
21. Compound 1g: see Ref. 1
22. 4 (322.44): C, 70.77; H, 9.38. Found: C, 70.65; H, 9.34
23. 4, and evaporated, yielding colorless or off-white, analytically pure solids
24. Compound 2a: D. Villemin, and M. Hammadi Synth. Commun. 26 1996 4337 4342
25. Compound 2b: D. Deffieux, I. Fabre, C. Courseille, and S. Quideau J. Org. Chem. 67 2002 4458 4465
26. Compound 2c: K. Freudenberg, and H.G. Müller Justus Liebigs Ann. Chem. 584 1953 40 53
27. Compounds 2d and 2e: F. Koelsch J. Am. Chem. Soc. 53 1931 304 305
28. +-I]; 105 (49) [ C 8 H 9 + ]; 77 (67) [ C 6 H 5 + ]
29. +): 413.1207. Found: 413.1224
30. 4, and evaporated. Phenols 3 were purified via column chromatography on silica with cyclohexane and EtOAc as eluents
31. O. Wolff, and S.R. Waldvogel Synthesis 2004 1303 1305
32. T. Shioiri, and S. Yamada Org. Synth. 1990 187 190
33. +): 297.1097. Found: 297.1061
34. Phenols 3 could not be separated from the by-products 4 by column chromatography. Therefore, 3e was purified by distillation in high vacuum