Abstract
Our ongoing study on cycloaddition reactions of dienes with different dienophiles afforded a great variety of derivatives with interesting molecular structures and electronic behavior. A new type of angularly annelated [2.2]paracyclophane (3) has been synthesize by the Diels–Alder reaction of 4-(2-propenyl[2.2]paracyclophane (1) and 1,4-benzoquinone (2) under high pressure conditions. The structure determination of this compound has been achieved by NMR measurements and semiempirical calculations.
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a) Minuti, L.; Taticchi, A.; Marrocchi, A.; Costantini, L.; Gacs-Baitz, E., Tetrahedron: Asymmetry 2001, 12, 1179. (b) Minuti, L.; Taticchi, A.; Marrocchi, A.; Lanari, D.; Gacs-Baitz, E. Tetrahedron: Asymmetry 2002, 13, 1331.
Mitchell, R. H. Cyclophanes; Academic Press: New York, 1983; Vol. 1, p. 239.
Ernst, L., NMR Studies of Cyclophanes, In Prog. Nucl. Magn. Spectrosc. 2000, 37, 47.
(a) Minuti, L.; Taticchi, A.; Lanari, D.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron: Asymmetry 2003, 14, 2775. (b) Aly, A. A.; Mourad, A.-F. E., Tetrahedron 1993, 49, 7325.
a) Fringuelli, F.; Taticchi, A. Dienes in the Diels–Alder Reaction, Wiley: New York, 1990; b) Fringuelli, F.; Taticchi, A. Diels–Alder Reaction. Selected Pratical Methods, Wiley: New York, 2002.
Tobe, Y.; Takahashi, T.; Ishikawa T.; Yoshimura M.; Suwa, M.; Kobiro, K.; Kakiuchi, K.; Gleiter, R. J. Am. Chem. Soc. 1990, 112, 8889.
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Gács-Baitz, E., Egyed, O., Taticchi, A. et al. Structure Determination of an Unusual [2.2]paracyclophane Derivative by NMR Spectroscopy. Struct Chem 16, 581–585 (2005). https://doi.org/10.1007/s11224-005-6098-1
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DOI: https://doi.org/10.1007/s11224-005-6098-1