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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 strain-induced C-C oxidative addition of norbornadiene is described, mediated by a dinuclear Ni complex, which also serves as a catalyst for the carbonylative rearrangement of nor Bornadiene to form a bicyclo[3.3.0] product.
Abstract: Single bonds between carbon atoms are inherently challenging to activate using transition metals; however, ring-strain release can provide the necessary thermodynamic driving force to make such processes favorable. In this report, we describe a strain-induced C–C oxidative addition of norbornadiene. The reaction is mediated by a dinuclear Ni complex, which also serves as a catalyst for the carbonylative rearrangement of norbornadiene to form a bicyclo[3.3.0] product.
33 citations
TL;DR: In this paper, the aza-Diels-Alder reaction of 4-phosphinyl- and 4phosphonyl-1,2-diaza-1-3-butadienes with styrene, cyclopentadiene, dihydrofuran and norbornadiene is reported.
33 citations
TL;DR: In this paper, a polyaddition of BNMA with bisphenol A diglycidyl ether (BPGE) was carried out using tetrabutylammonium bromide as a catalyst in NMP at 100 °C for 24 h, a polymer with a number average molecular weight of 18 000 was obtained in 91% yield.
Abstract: N,N'-Bis[(3-carboxynorbornadien-2-yl)carbonyl]methylenedianiline (BNMA) was synthesized in 87 % yield by the reaction of 2,5-norbornadiene-2,3-dicarboxylic acid anhydride with 4,4'-methylene-dianiline. Other dicarboxylic acid derivatives containing norbornadiene (NBD) residues were also prepared by the reaction of 2,5-NBD-2,3-dicarboxylic acid anhydride with certain diamines. When the polyaddition of BNMA with bisphenol A diglycidyl ether (BPGE) was carried out using tetrabutylammonium bromide as a catalyst in NMP at 100 °C for 24 h, a polymer with a number average molecular weight of 18 000 was obtained in 91% yield. Polyadditions of other NBD dicarboxylic acid derivatives with BPGE were also performed under the same conditions. The reaction proceeded very smoothly to give the corresponding NBD poly(ester-amide)s in good yields. Furthermore, the photochemical reactions of the NBD poly-(ester-amide)s were evaluated in the film state or in solution. The photochemical valence isomerization of NBD residues in the polymer films proceeded smoothly to form the corresponding quadricyclane (QC) groups upon irradiation with sunlight. The photochemical reversion of the resulting QC groups in the polymer films proceeded efficiently by irradiation of 272 nm light. The stored energy in the QC groups of the polymers was evaluated to be about 84 kJ/mol by DSC measurement of the irradiated polymer films.
32 citations
TL;DR: In this article, the reaction of dimethyl sulfide ditriflate with alkenes leads to the corresponding sulfonium salts, and the dependence of the reaction course on the substrate structure is discussed.
32 citations
TL;DR: Sterically protected fused 1,2,3thiadiazole and 1, 2,3-selenadiazoles were heated with molten sulfur resulting in a ready formation of fused cyclopolysulfides, the photolysis of which in the presence of olefins afforded the cycloadducts via the initially formed 1 2-dithione and 1 2 -selenoxothione as discussed by the authors.
32 citations