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• W1995051730 endingPage "736" @default.
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• W1995051730 abstract "anti- and syn-[2.8]Metacyclophan-1-enes 3a, which are both conformationally rigid structures, were prepared in good yields by a McMurry cyclization of 1,8-bis(5-tert-butyl-3-formyl-2-methoxyphenyl)octane 2a. Similarly, McMurry cyclization of 1,10-bis(5-tert-butyl-2-methoxy-3-formylphenyl)decane 2b afforded (E)- and (Z)-[2.10]-metacyclophan-1-enes 3b in good yields. The assignment of the E and Z structures was confirmed by 1H-NMR analyses and single crystal X-ray diffraction studies. Bromination of (E)- and (Z)-3b with benzyltrimethylammonium tribromide affords exclusively the cis-adduct 4b to the bridged double bond. When treated with potassium tert-butoxide in refluxing HOBut at 80 °C for 3 h, bromine adduct meso-4b gave the dehydrobrominated product [2.10]metacyclophan-1-yne 6b in 93% yield, along with 1-bromo[2.10]metacyclophan-1-ene 5b in 7% yield; the same reaction with the bromine adduct dl-4b gave 29% 6b along with 5b in 71% yield. Similarly, anti- and syn-[2.8]metacyclophan-1-ynes 6a were also prepared by bromination of syn-[2.n]metacyclophan-1-ene syn-3a, followed by the dehydrobromination of the bromine adduct. The characterization and the reaction pathway of these products are discussed. The dynamics of the ring inversion and UV spectra are also presented." @default.
• W1995051730 created "2016-06-24" @default.
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• W1995051730 date "2001-01-01" @default.
• W1995051730 modified "2023-10-07" @default.
• W1995051730 title "Medium-sized cyclophanes. Part 57. Synthesis, conformations and stereodynamics of [2.n]metacyclophan-1-enes and their conversion to [2.n]metacyclophan-1-ynes" @default.
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• W1995051730 doi "https://doi.org/10.1039/b010205i" @default.
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