2000
DOI: 10.1002/1099-0690(200010)2000:20<3363::aid-ejoc3363>3.0.co;2-i
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New Adventures in the Synthesis of Hetero-Bridgedsyn-Facially Fused Norbornadienes (“[n]Polynorbornadienes”) and Their Topological Diversity

Abstract: Molecular Scaffolds formed by the linking of bicyclo[2.2.1]heptane (norbornane) subunits by sharing a common C 2bridge have great appeal to the molecular architect since modelling studies have shown that the syn-facially fused members have a curved topology. Furthermore, this curvature can be modified by replacement of the methylene bridge by heteroatom bridges (O, S, NR), and made rod-like by introducing a σ-bond between adjoining methylene bridges in sesquinorbornane subunits. This review presents synthetic … Show more

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Cited by 54 publications
(25 citation statements)
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“…Such scaffolds can be used to modify topology since molecular modelling shows that they are less curved than the compounds lacking the N,N-methanobridge. 11 The N-bridges are locked into a geometry corresponding to the highly disfavoured syn,syn-invertomer geometry of diazasesquinorbornanes, a feature which can be exploited in the molecular design of polarofacial scaffolds. The neighbouring group participation route is not restricted to N-C-N bridges and other examples will be reported in due course.…”
Section: Methodsmentioning
confidence: 99%
“…Such scaffolds can be used to modify topology since molecular modelling shows that they are less curved than the compounds lacking the N,N-methanobridge. 11 The N-bridges are locked into a geometry corresponding to the highly disfavoured syn,syn-invertomer geometry of diazasesquinorbornanes, a feature which can be exploited in the molecular design of polarofacial scaffolds. The neighbouring group participation route is not restricted to N-C-N bridges and other examples will be reported in due course.…”
Section: Methodsmentioning
confidence: 99%
“…1,3,4-oxadiazole is commonly utilized pharmacophore has been subjected to extensive study in the recent years due to their metabolic profile and ability to engage in hydrogen bonding with receptor site. 1,3,4-Oxadiazoles are an important class of heterocyclic compounds with a wide range of biological activities such as antiviral [10], antimicrobial [11], antineoplastic [12], fungicidal [13], anticancer [14,15], inhibition of tyrosinase [16], They are also useful intermediates in organic synthesis [17] and widely employed as electron transporting and hole-blocking materials.…”
Section: Introductionmentioning
confidence: 99%
“…The polynorbornanes (such as 4 , Scheme ) are under research for use in nanotechnology, energy, and electron transfer, as anticancer bis‐intercalators and self‐assembled systems . Other possibilities for their use exist in the production of new materials and host/guest chemistry.…”
Section: Introductionmentioning
confidence: 99%
“…Diels–Alder (DA) reactions were the main way used to make polynorbornanes until the discovery of “Alkene Cyclobuane Epoxide (ACE)‐couplingˮ and its nitrogen counterpart “aza ACE‐coupling.ˮ DA approach was successful in producing various sesquinorbornanes but limited in producing larger polynorbornanes . The main drawback in using DA cycloadditions to produce polynorbornanes was that the reaction exhibited little stereocontrol.…”
Section: Introductionmentioning
confidence: 99%