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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.


Papers
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Journal ArticleDOI
TL;DR: NMR and computational studies give insight into the mechanism of the reactions and reveal the labile nature of the phosphorus–boron bond in 2, which is also suggested by detailed NMR spectroscopic studies on this compound.
Abstract: Salt metathesis of 1-methyl-2,4,6-triphenylphosphacyclohexadienyl lithium and chlorobis(pentafluorophenyl)borane affords a 1-phospha-7-bora-norbornadiene derivative 2. The C≡N triple bonds of nitriles insert into the P-B bond of 2 with concomitant C-B bond cleavage, whereas the C≡C bonds of phenylacetylenes react with 2 to form λ4 -phosphabarrelenes. Even though 2 must formally be regarded as a classical Lewis adduct, the C≡N and C≡C activation processes observed (and the mild conditions under which they occur) are reminiscent of the reactivity of frustrated Lewis pairs. Indeed, NMR and computational studies give insight into the mechanism of the reactions and reveal the labile nature of the phosphorus-boron bond in 2, which is also suggested by detailed NMR spectroscopic studies on this compound. Nitrile insertion is thus preceded by ring opening of the bicycle of 2 through P-B bond splitting with a low energy barrier. By contrast, the reaction with alkynes involves formation of a reactive zwitterionic methylphosphininium borate intermediate, which readily undergoes alkyne 1,4-addition.

2 citations

Journal ArticleDOI
TL;DR: Using an optimized amount of CsF for the generation of the arynes from silylaryl triflates, a range of benzo-fused norbornadiene derivatives is formed by cycloaddition with 6- or 6,6-substituted pentafulvenes as mentioned in this paper.
Abstract: Using an optimized amount of CsF for the generation of the arynes from silylaryl triflates, a range of benzo-fused norbornadiene derivatives is formed by cycloaddition with 6- or 6,6-substituted pentafulvenes.

2 citations

Journal ArticleDOI
TL;DR: The role of the rigid matrix environment on selectivity of the photochemical reaction is discussed in this article, where the photoproduct, representing a single species, was assigned to quadricyclane.

2 citations

Journal ArticleDOI
TL;DR: In this article, MM2 calculations were used to elucidate energies and structures of possible reaction products in olefin metathesis of 2,3-dimethylnorbornadiene.
Abstract: Molecular mechanics calculations (MM2) are used to elucidate energies and structures of possible reaction products in olefin metathesis of 2,3‐dimethylnorbornadiene. The comparison of experimental and calculational results concerning norbornadiene itself shows excellent agreement both in energy and structure. The predicted isomers of lowest energy in a series of three different reaction products seem highly reliable and will lead to a more precise interpretation of the olefin metathesis reaction and the resulting product distribution. Some sixty different isomers have been considered and structures and energies are given. Nonplanarity of double bonds and van der Waals repulsions of closely related hydrogen atoms in polycyclic cycloolefins are considered in some detail. In order to reduce computing time and efforts in obtaining starting coordinates, a computer program for some dimeric structures was devised, which can combine minimized structures stemming from MM2 calculations.

2 citations

Patent
03 Sep 1984
TL;DR: In this article, a 0.1-10wt% norbornadiene deriv. expressed by the formula is contained in a photo-sensitive resin resin, which forms a pi-complex with a metal.
Abstract: PURPOSE:To improve adhesion of a resist to metal in a dry film photoresist to be used for the manufacture of printed circuit boards by incorporating a specified norbornadiene deriv. to the photosensitive resin of the photoresist. CONSTITUTION:0.1-10wt% norbornadiene deriv. expressed by the formula is contained in a photosensitive resin. Since the norbornadiene deriv. forms a pi- complex with a metal, the photosensitive resin contg. said deriv. as an effective component forms a picture image having excellent adhesion to metals such as Cu, Zn, Al. In the formula, R1, R2 are H, alkyl such as methyl, ethyl, etc., phenyl, alkoxy, or OH.

2 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202316
202240
202133
202040
201930
201829