Et3B, an Efficient Mediator for Xanthate Transfer Based Radical Processes
DOI:
https://doi.org/10.29356/jmcs.v51i4.1283Keywords:
Xanthate, triethylborane, radical addition, olefinsAbstract
Abstract. The triethylborane mediated intermolecular addition of diverse carbon radicals, derived from the corresponding xanthates, to allyl acetate (10b) and 4-allyl-1,2-dimethoxybenzene (10a) was studied in various solvents. In most cases, the product yields in wáter at room temperature were as good as, or better than, those obtained using 1,2-dichloroethane as the solvent. In contrast, ethanol in most cases was not a useful solvent in which to conduct these reactions.
Resumen. El trietilborano fue utilizado como iniciador de la reacción de adición intermolecular de diversos radicales alquilo derivados de los correspondientes xantatos al acetato de alilo (10b) y al 4-alil-1,2-dimetoxibenceno (10a). La reacción fue estudiada en diversos disolventes; en la mayoría de los casos, los rendimientos obtenidos en agua a temperatura ambiente fueron mejores que cuando se utilizó 1,2-dicloroetano como disolvente. En contraste, el etanol no fue un disolvente útil para llevar a cabo estas reacciones.
Downloads
References
2. Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547-2549.
3. Sibi, M. P.; Liu, P. R.; Ji, J. G.; Hajra, S.; Chen, J. X.; J. Org. Chem. 2002, 67, 1738-1745.
4. Isibashi, H.; Inomata, M.; Ohba, M.; Ikeda, M. Tetrahedron Lett. 1999, 40, 1149-1152.
5. a) Zard, S. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 672-685. b) Quiclet-Sire, B.; Zard, S. Z. J. Chin. Chem. Soc. 1999, 46, 139-145. c) Briggs, M. E.; Zard, S. Z. Synlett 2005, 334-336.
6. a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1986, 62, 143-147. b) Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415-3434. c) Perchyonok, V. T.; Schiesser, C. H. Tetrahedron Lett. 1998, 39, 5437-5438. c) Briggs, M. E.; Zard, S. Z. Synlett 2005, 334-336. d) Charrier, N.; Gravestock, D.; Zard, S. Z. Angew Chem. Int. Ed. 2006, 45, 6520-6523.
7. Guerrero, M. A.; Miranda, L. D. Tetrahedron Lett. 2006, 47, 2517-2520.
8. a) Li, C. –J. Chem. Rev. 1993, 93, 2023-2035. b) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751-2772.
9. Breslow, R. Acc. Chem. Res. 1991, 24, 159-164.
10 Gajewski, J. J. Acc. Chem. Res. 1997, 30, 219-225.
11. Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403-409.
12. Lambert, T. H.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 2792-2793.
13. Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. J. Am. Chem. Soc. 2005, 127, 12513-12515.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.