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dc.contributor.authorCai, Guangkeen_US
dc.contributor.authorChatterjee, Shreyamen_US
dc.contributor.authorHisaki, Ichiroen_US
dc.contributor.authorTobe, Yoshitoen_US
dc.date.accessioned2019-05-02T00:25:53Z-
dc.date.available2019-05-02T00:25:53Z-
dc.date.issued2019-03-01en_US
dc.identifier.issn0018-019Xen_US
dc.identifier.urihttp://dx.doi.org/10.1002/hlca.201800242en_US
dc.identifier.urihttp://hdl.handle.net/11536/151618-
dc.description.abstractIn search of 2,7-ethylene-bridged naphthalenophanes with desymmetrized naphthalene cores as inherently chiral cyclophanes, nucleophilic substitution of 1-bromo-7-(bromomethyl)-2-[(trimethylsilyl)methyl]naphthalene, a desymmetrized building block bearing an electrophilic group (CH2Br) and a masked nucleophilic functionality (CH2TMS) which can be activated by fluoride anion, was examined. As a result, in contrast to the case of parent naphthalenophanes wherein the smallest [2.2]naphthalenophane was obtained as the major product, only [2.2.2.2](2,7)-1-bromonaphthalenophane was obtained albeit in low yields, whereas the corresponding [2.2]- or [2.2.2]naphthalenophanes were not obtained. Though the [2.2.2.2]-1-bromonaphthalenophane can adopt four idealized geometries of different symmetry, among which three are inherently chiral, theoretical calculations predict that three conformers have almost equal energy and may equilibrate in solution. The X-ray crystallographic study shows that it adopts a C-2 conformation with anti,anti,anti orientation of the C-Br bonds at least as a major component in crystal.en_US
dc.language.isoen_USen_US
dc.subjectcyclophanesen_US
dc.subjectstereochemistryen_US
dc.subjectconformation analysisen_US
dc.subjectcyclizationen_US
dc.subjectnucleophilic substitutionen_US
dc.title[2.2.2.2](2,7)-1-Bromonaphthalenophane from a Desymmetrized Building Block Bearing Electrophilic and Masked Nucleophilic Functionalitiesen_US
dc.typeArticleen_US
dc.identifier.doi10.1002/hlca.201800242en_US
dc.identifier.journalHELVETICA CHIMICA ACTAen_US
dc.citation.volume102en_US
dc.citation.issue3en_US
dc.citation.spage0en_US
dc.citation.epage0en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000462096100005en_US
dc.citation.woscount0en_US
Appears in Collections:Articles