期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 1, 页码 27-35出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo702151n
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资金
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0718117] Funding Source: National Science Foundation
[GRAPHICS] 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[1(4)]metacyclophane and the related polymer were the primary products (similar to 60% overall yield); aza[1(n)]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 (D-2d) and 1,3,5-alternate (S-6) conformations in solution on NMR time scale at low temperatures were found for macrocycles with n = 4 and n = 6, respectively; the barrier for ring inversion was considerably lower for the larger macrocycle.
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