Synthesis of [1.1.1.1]Metacyclophane Macrocycle

Andrzej Rajca, Raghavakaimal Padmakumar, Donald J. Smithhisler, Shailesh R. Desai, Charles R. Ross, John J. Stezowski

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Additions of organodilithium reagents to dialdehydes allow for construction of [1.1.1.1]metacyclophane macrocycle in ∼40% yield in the ring forming step, without resort to standard high dilution techniques. The present methodology is complementary to the conventional condensations leading to phenol- and resorcinol-based cyclotetramers.

Original languageEnglish (US)
Pages (from-to)7701-7703
Number of pages3
JournalJournal of Organic Chemistry
Volume59
Issue number25
DOIs
StatePublished - Dec 1 1994

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Phenol
Dilution
Condensation
resorcinol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Rajca, A., Padmakumar, R., Smithhisler, D. J., Desai, S. R., Ross, C. R., & Stezowski, J. J. (1994). Synthesis of [1.1.1.1]Metacyclophane Macrocycle. Journal of Organic Chemistry, 59(25), 7701-7703. https://doi.org/10.1021/jo00104a027

Synthesis of [1.1.1.1]Metacyclophane Macrocycle. / Rajca, Andrzej; Padmakumar, Raghavakaimal; Smithhisler, Donald J.; Desai, Shailesh R.; Ross, Charles R.; Stezowski, John J.

In: Journal of Organic Chemistry, Vol. 59, No. 25, 01.12.1994, p. 7701-7703.

Research output: Contribution to journalArticle

Rajca, A, Padmakumar, R, Smithhisler, DJ, Desai, SR, Ross, CR & Stezowski, JJ 1994, 'Synthesis of [1.1.1.1]Metacyclophane Macrocycle', Journal of Organic Chemistry, vol. 59, no. 25, pp. 7701-7703. https://doi.org/10.1021/jo00104a027
Rajca A, Padmakumar R, Smithhisler DJ, Desai SR, Ross CR, Stezowski JJ. Synthesis of [1.1.1.1]Metacyclophane Macrocycle. Journal of Organic Chemistry. 1994 Dec 1;59(25):7701-7703. https://doi.org/10.1021/jo00104a027
Rajca, Andrzej ; Padmakumar, Raghavakaimal ; Smithhisler, Donald J. ; Desai, Shailesh R. ; Ross, Charles R. ; Stezowski, John J. / Synthesis of [1.1.1.1]Metacyclophane Macrocycle. In: Journal of Organic Chemistry. 1994 ; Vol. 59, No. 25. pp. 7701-7703.
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