2001
DOI: 10.1002/1099-0690(200107)2001:14<2743::aid-ejoc2743>3.0.co;2-s
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Some Investigations on [6]Metacyclophanes

Abstract: 6]Metacyclophanes 2 with chlorine or fluorine substituents have been synthesized by a novel, convenient version of the base-catalyzed double elimination of hydrogen chloride from the corresponding halopropellanes 7. Conformational analysis by 1 H and 13 C NMR spectroscopy revealed remarkable analogies of certain partial structures of the hexamethylene bridge of 2 with the known exo and endo conformers of [5]metacyclophanes 1. The Diels−Alder reactivity of 2 to-

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Cited by 5 publications
(4 citation statements)
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“…15 However, broad signals of the benzylic protons of 5 were observed by 1 H NMR analysis at room temperature, which suggests that 5 is achiral as a result of rapid ring flipping (Scheme 6).…”
Section: Enantioselective Synthesis Of Planar Chiral Metacyclophanes mentioning
confidence: 99%
“…15 However, broad signals of the benzylic protons of 5 were observed by 1 H NMR analysis at room temperature, which suggests that 5 is achiral as a result of rapid ring flipping (Scheme 6).…”
Section: Enantioselective Synthesis Of Planar Chiral Metacyclophanes mentioning
confidence: 99%
“…4 At room temperature, if the hexamethylene chain of 3 resides at one side of the aromatic ring (no ring flip to the other side), 3 can exhibit the planar-chirality. 8 However, the broad signals of the benzylic protons of 3 were observed by 1 H NMR analysis, which suggests the ring flip at room temperature.…”
mentioning
confidence: 97%
“…9 Shinokubo, Oshima, and coworker realized this type of macrocyclization using reactive triynes bearing hydrogens at two alkyne termini in an aqueous-organic biphasic system, which diminished the formation of undesired intermolecular reaction products. 5e However, only [9] and [10]metacyclophanes were obtained as minor products along with the major orthocyclophanes, and [7] and [8]metacyclophanes possessing short ansa chains were not obtained. 5e,10 Furthermore, the intramolecular cyclotrimerization of less reactive triynes bearing substituents at two alkyne termini have not been realized to date.…”
mentioning
confidence: 99%
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