Special Issue Reviews and Accounts ARKIVOC 2007 (ii) 54-120 Treatment of 443 with DMSO, NaCl and water (140oC, 4 h) led to 444 (quantitatively). A rational mechanism is proposed.233 CO2Me MeO2C CO2Me O OH O O CO2Me HO MeO2C CO2Me CO2Me MeO2C 443 444 3. Conclusions Dealkoxycarbonylations of a wide variety of substrates have been accomplished using NaCN, NaCl or LiCl and water in dipolar aprotic solvents such as DMSO and DMF. This procedure will continue to be useful in the dealkoxycarbonylations of activated ester functionalities. 4. References 1. Krapcho, A. P. Synthesis 1982, 893. 2. Backvall, J-E.; Vagberg, J-O.; Granberg, K. L. Tetrahedron Lett. 1989, 30, 617. 3. Ito, S.; Saito, N.; Hatekeda, K.; Goto, T.; Ikushima, Y.; Asano, T. Bull. Chem. Soc. Jpn. 1984, 57, 2015. 4. Curran, D. P.; Zhang, Q. Adv. Synth. Catal. 2003, 345, 329. 5. Kolasa, A. J. Fluorine Chem. 1987, 36, 29. 6. Toro, A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526. 7. Bram, G.; Cabaret, D.; Welvart, Z.; Geraghty, N. W. A.; Garvey, J. Tetrahedron Lett. 1988, 29, 4615. 8. Dolle, R. E.; Osifo, K. I. Li, C.-S. Tetrahedron Lett. 1991, 32, 5029. 9. Langlois, M.; Yang, D.; Soulier, J.-L.; Florac, C. Synth. Commun. 1992, 22, 3115. 10. Lastdrager, B.; Timmer, M. S. M.; van der Marel, G. A.; Overkleeft, H. S. Tetrahedron Lett. 2005, 46, 6195. 11. Austad, B. C.; Hart, A. C.; Burke, S. D. Tetrahedron 2002, 58, 2011. 12. Hok, S.; Schore, N. E. J. Org. Chem. 2006, 71, 1736. 13. Pellissier, H.; Santelli, M. Tetrahedron 1996, 52, 9093. 14. Gonzalez, G. I.; Zhu, J. J. Org. Chem. 1999, 64, 914. 15. Back, T. G.; Wulff, J. E. Angew. Chem. Int. Ed. 2004, 43, 6493. 16. Murali, D.; Rao, G. S. Krishna, Indian J. Chem. 1987, 26B, 158. 17. Morgan, T. K,.Jr.; Lis, R.; Marisca, A. J.; Argentieri, T. M.; Sullivan, M. E.; Wong, S. S. J. Med. Chem. 1987, 30, 2259. ISSN 1424-6376 Page 111 ©ARKAT USA, Inc.
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