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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 11-12
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Original Articles

Reaction of [Methoxy(Phenylthio)Methyl]Trihethylsilane with Arenes and Alk-1-Enes in the Presence of Lewis Acid

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Pages 2213-2218 | Received 21 Oct 1988, Published online: 24 Oct 2006

References

  • Trost , B. M. and Miller , C. H. 1975 . J. Am. Chem. Soc. , 97 : 7182
  • Otera , J. 1988 . Synthesis , : 95
  • Nishiyama , H. , Narimatsu , S. , Sakuta , K. and Itoh , K. 1982 . J. Chem. Soc., Chem. Commun. , : 459
  • Sato , T. , Okura , S. , Otera , J. and Nozaki , H. 1987 . Tetrahedron Lett. , 28 : 6299
  • Magnus , P. D. and Roy , G. 1979 . J. Chem. Soc., Chem. Commun. , : 822
  • Carey , F. A. and Court , A. S. 1972 . J. Org. Chem. , 37 : 939
  • Ager , D. J. 1981 . Tetrahedron Lett. , 22 : 2923
  • Hackett , S. and Livinghouse , T. 1986 . J. Org. Chem. , 51 : 879
  • We have found an alternative route to (1) which consists in the reaction of [phenylthio{chloro)methyl]trimethylsilanes in excess MeOH in the presence of Et3N; unpublished results.
  • Use of 2 equivalents of Lewis acid and (2) also gave same product (3).
  • Representative spectral data of 3. [phenylthio(4-methoxy-phenyl)methyl]trimethylsilane: 1H NMR (COCl3) δ 0.13 (9H, s), 3.66 (1H, s), 3.70 (3H, s), 6.62–6.80 (2H, m) and 6.90–7.25 (7H. m); IR (neat) 2960, 1505, 1245, 840 cm−1, m/z(%) 302 (M+, 19.8), 193 (78.1), 165(100).
  • Ishibashi , H. , Nakatani , H. , Umei , Y. , Yamamoto , W. and Ikeda , M. 1987 . J. Chem. Soc. Perkin Trans. , 1 : 589 [phenyl(phenyllio)methyl]trimethylsilane could not be obtained from the reaction of [phenylthio(chloro)methyl] trimethylsilane
  • Ishibashi , H. , Komatsu , H. , Maruyama , K. and Ikeda , M. 1985 . Tetrahedron Lett. , 26 : 5791 and references cited therein. For other ene type reactions of a-thiocarbocation, see:
  • Ishibashi , H. , Sato , T. , Irie , M. , Ito , M. and Ikeda , M. 1987 . J. Chem. Soc., Perkin Trans. 1 , : 1095
  • Representative spectral data of 5, [1-(phenylthio)hept-3-enyUtrimethylsilane: 1H NMR (CDCl3) δ 0.14 (9H. s), 0.70–2.54 (10H, m). 5.28–5.59 (2H, m), 6.95–7.48 (5H, m); IR (neat) 2950, 1250, 835, 735 cm−1; m/z (%) 278 (M+, 14.6), 182 (69.1), 167(100).

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