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Original Articles

IMPROVED PROCEDURE FOR THE LARGE SCALE SYNTHESIS OF 1,2,3,4,4a,9b-HEXAHYDRODIBENZOTHIOPHENE

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Pages 169-173 | Received 16 Nov 1999, Accepted 22 Feb 2000, Published online: 12 Feb 2009

References

  • Bianchini , C. , Casares , J. A. , Meli , A. , Semau , V. , Vizza , F. and Sancez-Delagdo , R. A. 1997 . Polyhedron , 18 : 3099 b) J. J. Garcia, A. Arevalo, V. Montiel, F. Del Rio, B. Quiroz, H. Adams and P. M. Maitlis, Organometallics, 16, 3216(1997); c) C. Bianchini, M. V. Jimenez, A. Meli, S. Moneti, F. Vizza, V. Herrera and R. A. Sanchez-Delgado, ibid., 14, 2342(1995); d) V. Lamure-Meille, E. Schulz, M. Lemaire, and M. Vrinat, Appl. Catal., A, 131, 143(1995); e) A. Ishihara and T. Kabe, Ind. Eng. Chem. Res., 32, 753(1993); f) G. Singhal, R. L. Espino, J. E. Sobel and G. A. Huff, J. Catal., 67, 457(1981); g) G. Singhal, R. L. Espino and J. E. Sobel, ibid., 67, 446(1981).
  • Wristers , J. 1977 . J. Am. Chem. Soc. , 99 : 5051 These papers report the 1H NMR resonances of the title compound (5) as a series of multiplets without distinction as to the stereochemistry about the fused ringa. b) D. Derouane, J. N. Harvey and H. G. Viehe, Chem. Commun., 993 (1995).
  • The thermodynamic properties will be reported by personnel of the National Institute for Petroleum and Energy Research, Bartlesville, OK 74005.
  • Wintemitz , F. , Antia , N. J. , Tumlirova , M. M. and Lachazette , R. 1956 . Bull. Soc. Chim. Fr. , : 1817 Synthesis of 2; b) Synthesis of 5 from 2; R. B. Mitra, and B. D. Tilak;, J. Sci. Industr. Res., 15B, 573(1956).
  • Yields reported in reference 4 are yields of isolated compounds. Yields reported in this paper are for the purified compounds (> 99.9%).
  • Bordwell , F. G. , Lampert , B. and McKellin , W. H. 1949 . J. Am. Chem. Soc. , 71 : 1702
  • McKillop , A. and Kemp , D. 1989 . Tetrahedron , 45 : 3299
  • Ace Glass # 6436–265 and 13660–50. The need to repressurize the reaction flask could be eliminated with the use of a reservoir tank.
  • Spartan SGI 5.0.3 by Wavefunction, Inc. The actual values are 39.56 and 40.72 for the two cis-isomer conformers where the sulfur is axial and equatorial respectively and 168.62 for the trans-isomer.
  • Haasnoot , C. A. G. , DeLeeuw , F. A. A. M. and Altona , C. 1980 . Tetrahedron , 36 : 2783
  • Both ring juncture hydrogens appear as a quartet (even at 400 MHz) indicating equal coupling from the three adjacent hydrogens. The measured coupling constants to each hydrogen was 5.7 and 6.1 Hz. The smaller of the numbers was determined to be the proper coupling, J4a-9b. The cis-isomer has two low energy conformations; one in which the sulfur is axial to the cyclohexane ring and one in which the sulfur is equatorial. A rapid interconversion of the two conformations would account for the observed quartets for the juncture hydrogens.

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