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Norbornadiene
About: Norbornadiene is a research topic. Over the lifetime, 2389 publications have been published within this topic receiving 38603 citations.
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TL;DR: A family of enantiomerically pure (2R)-10-(alkylthio)isoborneols, specifically designed as chiral auxiliaries suitable for chirality transfer to cobalt in Pauson−Khand reactions, has been synthesized.
Abstract: A family of enantiomerically pure (2R)-10-(alkylthio)isoborneols [methylthio (1), neopentylthio (2), phenylthio (3)], specifically designed as chiral auxiliaries suitable for chirality transfer to cobalt in Pauson−Khand reactions, has been synthesized. The dicobalt hexacarbonyl complexes of the alkoxyacetylenes derived from these alcohols (10a−12a) can be converted to the rather stable, internally chelated, pentacarbonyl complexes 10b−12b by treatment with NMO. The intermolecular Pauson−Khand reactions of 10b−12b with strained olefins take place with synthetically useful rates at low temperatures (down to −20 °C), with high yields and diastereoselectivities: norbornene (77%; 92:8), norbornadiene (82%; 96:4), bicyclo[3.2.0]hept-6-ene (91%; 93:7). The major diastereomer of the adduct of 10b with norbornadiene, 14, has been used as the starting point for a synthesis of (S)-(−)-4-alkyl-2-cyclopentenones through a sequence consisting of completely diastereoselective conjugate addition, reductive cleavage with...
TL;DR: Norbornene and norbornadiene derivatives have been shown to react with aryl and vinyl halides in the presence of a palladium catalyst, formic acid, and tributylamine or piperidine to give hydroarylated and hydrovinylated derivatives in good to high yield.
Abstract: Norbornene and norbornadiene derivatives have been shown to react with aryl and vinyl halides in the presence of a palladium catalyst, formic acid, and tributylamine or piperidine to give hydroarylated and hydrovinylated derivatives in good to high yield. Extension of the reaction to the hindered α,β-unsaturated aldehydic system of myrtenal produced a monocyclic derivative through a palladium-catalyzed ring opening.
TL;DR: The chlorination of norbornadiene by CuCl2, TlCl3·4H2O, SbCl5, SeCl4, and VCl4 in CCl4 or CH3-CN afforded mainly trans-3,5-(1) and exo-cis 3,5-dichloronortricyclene (2).
Abstract: The chlorination of norbornadiene by CuCl2, TlCl3·4H2O, SbCl5, SeCl4, and VCl4 in CCl4 or CH3-CN afforded mainly trans-3,5-(1) and exo-cis-3,5-dichloronortricyclene (2). In the reaction with PbCl4, Cl2, SO2Cl2, and PCl5, appreciable amounts of exo-5-syn-7-(3) and/or exo-cis-5,6-dichloronorbornene (4) were obtained besides 1 and 2.
TL;DR: In this article, a mass spectral study of (norbornadiene)(acetylacetonato)rhodium derivatives showed that [Rh-norbornadene]- ions are more stable than [acacRh]- ions.
Abstract: 1.
A mass spectral study of (norbornadiene)(acetylacetonato)rhodium derivatives showed that [Rh-norbornadiene]+ ions are more stable than [acacRh]+ ions. The decomposition of the molecular ions of these compounds with cleavage of the metal-ligand bonds is accompanied by a series of hydrogen rearrangements due to the migration of a hydrogen atom from the ligands to the metal atom or another ligand.
2.
The greatest stability among the fragment ions, in which the bond of the metal atom with both ligands is retained, is found for ions characterized by a 16-electron shell of the rhodium atom and its oxidation state of +3.