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Miscellany

Synthesis and Characterization of Thiophenetriptyeene-8-sulfenic Acid

Pages 323-324 | Published online: 17 Mar 2008

REFERENCES

  • For reviews, see: Kice J. L. Adv. Phys. Org. Chem. , 1980 , 17 , 65 ; Hogg, D. R. Chemistry of sulfenic acids an esters, In The Chemistry of Sulfenic Acids and Their Derivatives; Patai S. Ed; Wiley: New York, 1990; p 361> .
  • Yoshimura T. Tsukurimichi E. Yamazaki S. Soga S. Shimasaki C. Hasegawa K. J. Chem. Soc., Chem. Commun. 1992 , 1337 ; Goto, K.; Tokitoh, N.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1124; Saiki, T.; Goto, K.; Tokitoh, N.; Okazaki, R. J. Org. Chem. 1996, 61, 2924 .
  • Ishii A. Kodachi M. Nakayama J. Hoshino M. J. Chem. Soc., Chem. Commun. 1991 , 751 . (b) Ishii, A.; Maeda, K.; Kodachi, M.; Aoyagi, N.; Kato, K.; Maruta, T.; Hoshino, M.; Nakayama, J. J. Chem. Soc., Perkin Trans. 1 in press .
  • Staab H. A. Walther G. Ann. 1962 , 657 , 98 .
  • Sulfenic acid 4: 1H NMR (400 MHz, CDCl3) δ 2.18 (s, 3H), 2.33 (s, 9H), 3.71 (s, 1H, SOH), 6.65 (s, 3H); 13C NMR (100.6 MHz, CDCl3) δ 14.8 (CH3), 15.3 (CH3), 50.2 (2xC), 119.6 (CH), 135.0 (C), 148.5 (C), 158.2 (C);IR (KBr) 3456 (O-H) cm−1.
  • Crystal data for 4: trigonal, P¯, a=20.340(3) Å, b=20.340(3) Å, c=10.028(2) Å, V=3593 Å3, Z = 8, R=0.0709, Rw=0.0861. Selected bond lengths and angles: C-S: 1.833(9) Å; S-O: 1.622(9) Å; ∠C-S-O: 102.3(5)°.

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