An efficient and green approach for the synthesis of vinyl aryl ethers in the presence of guanidine hydrochloride
A stereoselective procedure for vinyl aryl ether bond formation by direct coupling of dialkyl acetylenedicarboxylates and substituted phenols or naphthols under mild reaction conditions has been developed. Using guanidine hydrochloride as a new catalyst and water-acetone as green solvent, dialkyl acetylenedicarboxylates were reacted with substituted phenols or naphthols in room temperature to produce vinyl aryl ethers in good to excellent yields.
An efficient and green approach for the synthesis of vinyl aryl ethers in the presence of guanidine hydrochloride
A stereoselective procedure for vinyl aryl ether bond formation by direct coupling of dialkyl acetylenedicarboxylates and substituted phenols or naphthols under mild reaction conditions has been developed. Using guanidine hydrochloride as a new catalyst and water-acetone as green solvent, dialkyl acetylenedicarboxylates were reacted with substituted phenols or naphthols in room temperature to produce vinyl aryl ethers in good to excellent yields.
___
- Shostakovsky, M. F. Vinyl ethers, Akademie Nauk SSSR: Moscow: Russian, 1952.
- TroŞmov, B. A. Heteroatomic derivatives of acetylene: new polyfunctional monomers, reagents and intermediates, Nauka- Moscow: Russian, 1981.
- Tedeschi, R. J. Acetylene-based chemicals from coal and other natural resources, Marcel Dekker: New York, 1982.
- Longley, R. A. J.; Emerson, W. S. J. Am. Chem. Soc., 1950, 72, 3079-3081.
- Cope, A. C.; Dryden, H. L. J.; Howell, C. F. Org. Synth.; Wiley & Sons: New York, Collect. 1963.
- Allen, G. Comprehensie polymer science, Ed.; Pergamon Press: New York, 1989.
- Mark, H. F.; Bikales, N.; Overberger, C. G.; Menges, G. Encyclopedia of polymer science and engineering, 2nd ed.; Eds.; John Wiley: New York, 1989.
- Kojima, K.; Sawamoto, M.; Higashimura, T. Macromolecules, 1989, 22, 1552-1557.
- Jones, D. E.; Morris, R. O.; Vernon, C. A.; White, R. F. J. Chem. Soc. B, 1960, 2349-2366.
- Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc., 2002, 124, 1590-1591.
- Rhoads, S. J.; Chattopadhyay, J. K.; Waali, E. E. J. Org. Chem., 1970, 35, 3352-3358.
- Yamawaki, J.; Kawate, T.; Ando, T.; Hanafusa, T. Bull. Chem. Soc. Jpn., 1983, 56, 1885-1886.
- Nasiri, F.; Atashkar, B. Monatsh. Chem., 2008, 139, 1223-1227.
- Yavari, I.; Souri, S.; Sirouspour, M.; Djahaniani, H.; Nasiri, F. Synthesis, 2005, 11,1761-1764.
- Ramazani, A.; Rahimifard, M. Phosphorus, Sulfur Silicon Relat. Elem., 2006, 181, 2675-2678.
- Kodomari, M.; Sakamoto, T.; Yoshitomi, S. J. Chem. Soc., Chem. Commun. 1990, 9, 701-702.
- Baharfar, R; Taghizadeh, M. J.; Ahmadian, M.; Baghbanian, S. M. Chin. Chem. Lett., 2010, 21, 175-178.
- Baharfar, R.; Tajbakhsh, M.; Hamedaninejad, A; Hosseini, S. J. Chin. Chem. Lett., 2008, 19, 175-179.
- Anastas, P.T.; Warner, J.C. Green chemistry: theory and practice, Oxford University Press: Oxford, 2000.
- Costa, M.; Chiusoli, G. P.; Taffurelli, D.; Dalmonego, G. J. Chem. Soc., Perkin Trans., 1998, 1, 1541-1546.
- Kovacevic, B.; Maksic, Z. B. Org. Lett., 2001, 3, 1523-1526.
- Yamamoto, Y.; Kojima, S. The chemistry of amidines and imidates, Patai S, Rappoport Z, Eds.; John Wiley & Sons Inc: New York, 1991.
- Eliel, E. L.; Wilen, S. H. Stereochemistry of organic compounds, Wiley, New York, p 569, 1994.
- Stoermer, M. J.; Fairlie, D. P. Aust. J. Chem., 1995, 48, 677-686.
- Kauer, J. C.; Simmons, H. E. J. Org. Chem., 1968, 33(7), 2720-6.
- Gupta, R. K.; George, M. V. Tetrahedron., 1975, 31, 1263-1275.