Abstract
The title macrocycle 1 was synthesised in good yield (66%) by a one-pot condensation process from 2,3-bis(chloromethyl)-p-xylene andN,N′-ditosylethylendiamine. The macrocycle was found to undergo isomerization processes at elevated temperature on the NMR time scale (ΔG≠ = 87.8 kJ mol−1) and acts as a suitable host only for toluene. The FAB-MS spectra of1 is rich, and full of interesting and very diagnostic fragmentation pathways.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
F. Bottino, M. Di Grazia, P. Finocchiaro, F. R. Fronczek, A. Mamo, and S. Pappalardo:J. Org. Chem. 53, 3521 (1988).
S. Pappalardo, F. Bottino, P. Finocchiaro, A. Mamo, and F. R. Fronczek:J. Incl. Phenom. 5, 153 (1987).
S. Pappalardo, F. Bottino, P. Finocchiaro, and A. Mamo:J. Polym. Sci. Polym. Chem. Ed. 25, 1793 (1987).
A. Mamo, P. Finocchiaro, F. Bottino, and S. Pappalardo:J. Polym. Sci. Polym. Chem. Ed. 28, 2237 (1990).
P. Finocchiaro, A. Mamo, S. Pappalardo, W. Weissensteiner, and M. Widhalm:J. Chem. Soc. Perkin Trans. 2, 449 (1991).
J. von Meisenheimer:Lieb. Ann. Chem. 438, 217 (1924).
G. Montaudo, P. Finocchiaro, S. Caccamese, and F. Bottino:J. Am. Chem. Soc 93, 4208 (1971).
H. S. Gutowsky and C. H. Holm:J. Chem. Phys. 25, 1288 (1956).
S. Pappalardo:Org. Mass. Spectrom. 24, 258 (1989).
S. Failla and P. Finocchiaro:J. Chem. Soc. Perkin Trans. 2, 701 (1992).
R. Newkome, V. K. Gupta, and S. Pappalardo:Org. Mass. Spectrom. 19, 590 (1984).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Failla, S., Finocchiaro, P. Synthesis, characterization, NMR study and clathration ability of N,N′,N″,N″′-tetratosyl-8,11,21,24-tetramethyl-2,5,14,17,-tetraaza-[6.6]-paracyclophane. J Incl Phenom Macrocycl Chem 13, 361–367 (1992). https://doi.org/10.1007/BF01133235
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01133235