Cyclization of Olefinic Benzyl Ethers with Aryltellurium Trichlorides

References

• Cardillo , G. and Orena , M. 1990 . Tetrahedron , 46 : 3321
   Web of Science ®Google Scholar
• Campos , M. M. and Petragnani , N. 1959 . Tetrahedron Lett. , 11
   Google Scholar
• Paulmier , C. 1986 . “Selenium Reagents and Intermediates in Organic Synthesis” , Pergamon Press . See for example:
   Google Scholar
• Comasseto , J. V. and Petragnani , N. 1983 . Synth. Commun. , 13 : 889
   Web of Science ®Google Scholar
• Comasseto , J. V. , Ferraz , H. M.C. , Petragnani , N. and Brandt , C. A. 1987 . Tetrahedron Lett , 28 : 5611
   Web of Science ®Google Scholar
• Bergman , J. and Engman , L. 1981 . J. Amer. Chem. Soc. , 103 : 5196
   Web of Science ®Google Scholar
• Engman , L. 1989 . Organometallics , 8 : 1997
   Web of Science ®Google Scholar
• Hu , N. X. , Aso , Y. , Otsubo , T. and Ogura , F. 1989 . J. Org. Chein. , 54 : 4391
   Web of Science ®Google Scholar
• Hu , N. X. , Aso , Y. and Ogura , F. 1989 . J. Org. Chem. , 54 : 4398
   Web of Science ®Google Scholar
• D'Angelo , J. 1976 . Tetrahedron , 32 : 2979
   Web of Science ®Google Scholar
• Brown , H. C. and Krishnamurthy , S. 1979 . Tetrahedron , 35 : 567
   Web of Science ®Google Scholar
• Letsinger , R. C. , Traynhan , J. G. and Bobko , E. 1952 . J. Amer. Chem. Soc. , 74 : 399
   Web of Science ®Google Scholar
• Greene , T. W. 1981 . Protecting Groups in Organic Synthesis , New York : Wiley .
   Google Scholar
• Petragnani , N. and Comasseto , J. V. 1986 . Synthesis , 1
   Google Scholar
• Typical Procedure for the Cyclization of Unsaturated Alcohols with p-Phenoxyphenyltellurium Trichloride To a solution of the unsaturated alcohol (entry 1, Table 1; 0.156 g, 1 mmol) in anhydrous chloroform (15 ml), at room temperature was added p-phenoxyphenyltellurium trichloride (0.403 g, 1 mmol). An exothermic reaction occurred. After 5 min of stirring the reaction mixture turned limpid; then the solvent was evaporated in a rotatory evaporator and the residue was recrystallized from chloroform/petroleum ether: 0.50g (97%); m.p.: 108–110°C; I.R. (KBr): 1243; 1485; 1576; 1HNMR (CDCl3/TMS, δ): 0.85–1.26(m,6H); 1.48–2.11(m,3H); [3.14(d, J 8.5); 3.37(d, J 7.32)1H]; [3.86(d, J 7.4); 3.95 (d, J 7.32)2H]; 4.59–4.79(m,1H); 6.95–7.39(m,7H); 8.03(d, J 8.79, 2H); Anal, calcd. for C22H28Cl2O2Te: C, 50.52; H, 5.39. Found: C, 50.47; H, 5.05
   Google Scholar
• Typical Procedure for the Cyclization of Unsaturated Benzyl Ethers with p-Phenoxyphenyltellurium Trichloride A mixture of the benzyl ether (entry 2, Table 1; 0.246 g, 1 mmol) and p-phenoxyphenyltellurium trichloride (0.403 g, 1 mmol) in anhydrous chloroform (15 ml) was stirred for 30 min at room temperature, then the solvent was evaporated and the residue was filtered through a column of silica gel eluting with chloroform. Evaporation of the solvent in a rotatory evaporator followed by recrystallization of the residue from chloroform/petroleum ether and washing several times with petroleum ether gave 0.50 g (97%) of a product with identical physical characteristics of that obtained in the preceding experiment
   Google Scholar