Combination of tert-butoxycarbonyl and triphenylphosphonium protecting groups in the synthesis of substituted hydrazines

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2297-2299

  Tšubrik, Olga ^a   Mäeorg, Uno ^a  

^a UNIVERSITY OF TARTU   (Estonia)

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EID: 0001296660     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0160856     Document Type: Article

References (21)

1. (a) Mäeorg, U.; Grehn, L.; Ragnarsson, U. Angew. Chem. 1996, 108, 2802-2803; Angew. Chem., Int. Ed. Engl. 1996, 35, 2626-2627.
2. (a) Mäeorg, U.; Grehn, L.; Ragnarsson, U. Angew. Chem. 1996, 108, 2802-2803; Angew. Chem., Int. Ed. Engl. 1996, 35, 2626-2627.
3. (b) Mäeorg, U.; Ragnarsson, U. Tetrahedron Lett. 1998, 39, 681-684.
4. (c) Mäeorg, U.; Pehk, T.; Ragnarsson, U. Acta Chem. Scand. 1999, 53, 1127-1133.
5. (d) Grehn, L.; Lönn, H.; Ragnarsson, U. Chem. Commun. 1997, 1381-1382.
6. (e) Grehn, L.; Nyasse, B.; Ragnarsson, U. Synthesis 1997, 1429-1432.
7. (f) Brosse, N.; Pinto, M.-F.; Jamart-Gregoire, B. Tetrahedron Lett. 2000, 41, 205-207.
8. (g) Brosse, N.; Pinto, M.-F.; Jamart-Gregoire, B. J. Org. Chem. 2000, 65, 4370-4374.
9. (h) Brosse, N.; Pinto, M.-F.; Bodiguel, J.; Jamart-Gregoire, B. J. Org. Chem. 2001, 66, 2869-2873.
10. (a) Zimmer, H.; Singh, G. J. Org. Chem. 1963, 28, 483-486.
11. (b) Zimmer, H.; Jayawant, M.; Gutsch, P. J. Org. Chem. 1970, 35, 2826-2828.
12. (c) Cristau, H. J.; Garcia, C.; Kadoura, J.; Torreilles, E. Phosphorus, Sulfur, Silicon Relat. Elem. 1990, 49/50, 151-154.
13. (a) Zimmer, H.; Singh, G. J. Org. Chem. 1964, 29, 1579-1581.
14. (b) Barluenga, J.; Merino, I.; Viña, S.; Palacios, F. Synthesis 1990, 398-400.
15. (c) Bestmann, H. J.; Göthlich, L. Liebigs Ann. Chem. 1962, 655, 1-19.
16. (a) Walker, C. C.; Shechter, H. J. Am. Chem. Soc. 1968, 90, 5626-5627.
17. (b) Merrill, G. B.; Shechter, H. Tetrahedron. Lett. 1975, 4527-4530.
18. (c) Frøyen, P. A. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 57, 11-15.
19. PC = 10.9), 137.0 (s, Ph), 158.2 (CO).
20. 2 1:7). An additional amount of product (0.191 g, pure by TLC) was precipitated by adding ether to the original THF solution, and thus the overall yield was 76%.
21. Stafford, J. A.; Brackeen, M. F.; Karanewsky, D. S.; Valvano, N. L. Tetrahedron Lett. 1993, 34, 7873-7876.