Synthesis of multilayered [3.3](3,5)pyridinophanes

Masahiko Shibahara, Motonori Watanabe, Kazuhiro Aso, Teruo Shinmyozu

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Two- to four-layered [3.3](3,5)pyridinophanes (PyPs) have been synthesized by the (4-tolylsulfonyl)methyl isocyanide (TosMIC) method. The coupling reaction between 3,5-bis[2-iso-cyano-2-(4-tolylsulfonyl)ethyl]pyridine (TosMIC adduct) and bis(chloromethyl) or tetrakis(bromomethyl) compounds in the presence of sodium hydride in N,N-dimethylformamide or sodium hydroxide and tetrabutylammonium iodide under high-dilution conditions gave the two-layered dione or three- and four-layered tetraones. Wolff-Kishner reduction of the ketones afforded the desired two- to four-layered [3.3](3,5)PyPs. The structure of the dione units take an anti geometry whereas the cyclophane units take a syn geometry in solution.

Original languageEnglish
Article numberF15008SS
Pages (from-to)3749-3754
Number of pages6
JournalSynthesis
Issue number23
DOIs
Publication statusPublished - Dec 1 2008

Fingerprint

Sodium
Dimethylformamide
Sodium Hydroxide
Geometry
Ketones
Hydrides
Pyridine
Dilution
methylisonitrile
sodium hydride
tetrabutylammonium
pyridine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Shibahara, M., Watanabe, M., Aso, K., & Shinmyozu, T. (2008). Synthesis of multilayered [3.3](3,5)pyridinophanes. Synthesis, (23), 3749-3754. [F15008SS]. https://doi.org/10.1055/s-0028-1083633

Synthesis of multilayered [3.3](3,5)pyridinophanes. / Shibahara, Masahiko; Watanabe, Motonori; Aso, Kazuhiro; Shinmyozu, Teruo.

In: Synthesis, No. 23, F15008SS, 01.12.2008, p. 3749-3754.

Research output: Contribution to journalArticle

Shibahara, M, Watanabe, M, Aso, K & Shinmyozu, T 2008, 'Synthesis of multilayered [3.3](3,5)pyridinophanes', Synthesis, no. 23, F15008SS, pp. 3749-3754. https://doi.org/10.1055/s-0028-1083633
Shibahara M, Watanabe M, Aso K, Shinmyozu T. Synthesis of multilayered [3.3](3,5)pyridinophanes. Synthesis. 2008 Dec 1;(23):3749-3754. F15008SS. https://doi.org/10.1055/s-0028-1083633
Shibahara, Masahiko ; Watanabe, Motonori ; Aso, Kazuhiro ; Shinmyozu, Teruo. / Synthesis of multilayered [3.3](3,5)pyridinophanes. In: Synthesis. 2008 ; No. 23. pp. 3749-3754.
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