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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 1-2
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Original Articles

Preparation and Cyclization of Aryloxyacetaldehyde Acetals; A General Synthesis of 2,3-Unsubstituted Benzofurans

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Pages 257-265 | Received 16 May 1988, Published online: 24 Oct 2006

References

  • Rene , L. and Royer , R. 1973 . Bull. Chim. Soc. Fr. , : 2355
  • Darling , S. D. and Wills , K. D. 1967 . J. Org. Chem. , 32 : 2794
  • Birkinshaw , J. H. , Chaplen , P. and Findlay , W. P. K. 1957 . Biochem J. , 66 : 188
  • Elderfield , R. C. and Meyer , V. B. 1951 . Heterocyclic Compounds , Edited by: Elderfield , R. C. Vol. 2 , 3 – 16 . New York : John Wiley & Sons .
  • Fiesselmann , H. and Ribka , J. 1956 . Chem. Ber. , 89 : 40
  • Kawase , Y. 1970 . Chem. Ind. , : 687
  • Tarbell , D. 1961 . J. Am. Chem. Soc. , 83 : 3096
  • Bradsher , C. 1946 . Chem. Rev. , 38 : 447
  • Rene , L. , Buisson , J. and Royer , R. 1975 . Bull. Soc. Chim. Fr. , : 2763
  • Rene , L. , Royer , R. and Demepseman , P. 1970 . Bull. Soc. Chim. Fr. , : 3740
  • Worden , L. , Kaufman , K. , Weiss , J. and Schaff , T. 1969 . J. Org. Chem. , 34 : 2311
  • Onishi , Y. , Doi , Y. and Nakanishi , T. 1984 . Chem. Pharm. Bull. , 32 : 4260
  • Hirota , T. 1986 . J. Het. Chem. , 23 : 1347
  • Stoermer , R. 1900 . Ann. , 312 : 237
  • Spagnola , R. , Tiecco , M. and Tundo , A. 1972 . JCS Perkin I , : 556
  • Unsuccessful cyclization conditions included both Lewis acids (SnCl2, AlCl3, BF3, FeCl3, and ZnCl2) and protic acids (H2SO4, TFA, dichloroacetic acid, oxalic acid, HCl, and p-toluene sulfonic acid). Attempted cylcization with P2O5 in the absence of phosphoric acid was also unsuccessful.
  • As a reagent for cyclodehydration polyphosphoric acid has found numerous applications in the synthesis of a variety fo aromatic and heteroaromatic systems16,17
  • Popp , F. D. and McEwen , W. E. 1958 . Chem. Rev. , 58 : 321
  • Fieser , L. F. and Fieser , M. 1967 . Reagents for Organic Synthesis , 894 – 905 . New York : John Wiley & Sons .

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