Synthesis, structure, and conformation of aza[1n]metacyclophanes

Matthew Vale, Maren Pink, Suchada Rajca, Andrzej Rajca

Research output: Contribution to journalArticle

55 Scopus citations

Abstract

(Chemical Equation Presented) N-Benzyl substituted aza[1 n]metacyclophanes (n = 4, 6, 8, and 10) were prepared in overall 40% isolated yields via Pd-catalyzed aminations. Analyses of the reaction mixtures showed that aza[14]metacyclophane and the related polymer were the primary products (∼60% overall yield); aza[1n]metacyclophanes up to n = 14 and linear oligomers with up to 20 nitrogen atoms (with at least three types of end groups) were detected. Macrocyclic structures for n = 4, 6, and 10 were confirmed by X-ray crystallography. 1,3-Alternate (D2d) and 1,3,5-alternate (S6) conformations in solution on NMR time scale at low temperatures were found for macrocycles with n = A and n = 6, respectively; the barrier for ring inversion was considerably lower for the larger macrocycle.

Original languageEnglish (US)
Pages (from-to)27-35
Number of pages9
JournalJournal of Organic Chemistry
Volume73
Issue number1
DOIs
StatePublished - Jan 4 2008

ASJC Scopus subject areas

  • Organic Chemistry

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