Medium-sized Cyclophanes. Part 44.1 Synthesis and Stereochemical Assignments of 9-Substituted 2,11-Dithia[3.3]metacyclophanes

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Takehiko Yamato, Mitsuaki Shigekuni, Hidetsugu Kunugida and Yoshiaki Nagano


Abstract

Various syn- and anti-9-substituted 2,11-dithia[3.3]metacyclophanes are obtained by the coupling reaction of the corresponding 2,6-bis(bromomethyl)benzenes and 1-substituted 2,6-bis(sulfanylmethyl)-4-tert-butylbenzenes under highly diluted conditions in 10% ethanolic KOH in the presence of a small amount of NaBH4.


References

  1. Part 43: T. Yamato, H. Kamimura, T. Furukawa, F. Zhang and Y. Nagano, J. Org. Chem., submitted for publication Search PubMed.
  2. K. Meurer and F. Vögtle, Top. Curr. Chem., 1985, 127, 1 CAS.
  3. (c)F. Vögtle, Cyclophane Chemistry, Wiley, Chichester, 1993 Search PubMed.
  4. (a) R. H. Mitchell and V. Boekelheide, Tetrahedron Lett., 1970, 1197 Search PubMed.
  5. F. Vögtle and L. Schunder, Chem. Ber., 1969, 102, 2677.
  6. M. Tashiro and T. Yamato, Org. Prep. Proced. Int., 1981, 13, 1 CAS.
  7. (a) M. Tashiro and T. Yamato, J. Org. Chem., 1981, 46, 1543 CrossRef CAS; (b) M. Tashiro, K. Koya and T. Yamato, J. Am. Chem. Soc., 1982, 104, 3707 CrossRef CAS; (c) M. Tashiro, A. Tsuge, T. Sawada, T. Makishima, S. Horie, T. Arimura, S. Mataka and T. Yamato, J. Org. Chem., 1990, 55, 2404 CrossRef CAS.
  8. M. Nishio and M. Horita, Tetrahedron, 1989, 45, 7201 CrossRef CAS.
  9. (g) K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi and Y. Aoyama, J. Am. Chem. Soc., 1993, 115, 2648 Search PubMed.
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