Synthesis and reactions of 5,6,11,12-tetrahydro-5,12;6,11-diethenodibenzo-[α,e]cyclo-octene (pp′-dinaphthalene)

Tobe, Yoshito; Hirata, Fumiaki; Nishida, K.; Fujita, Hisashi; Kawasaki, Koji; Odaira, Yoshinobu

doi:10.1039/c39810000786

Cited by 9 publications

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“…The 1,3 or meta addition is only observed with benzene. 182 The examples given below (89)(90)(91)(92)(93)(94)(95)(96)(97)(98)(99)(100)(101)(102)(103)(104) are additions occur in the substituted naphthalene ring and are almost exclusively 1,4. Structure 88b is based on X-ray crystal structure analysis,173 and the observed regiochemistry apparently rules out significant biradical or zwitterionic character in the transition state for addition.…”

Section: Phmentioning

confidence: 99%

Photoadditions of aromatic compounds

McCullough¹

1987

Chem. Rev.

185

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Section: Phmentioning

confidence: 99%

Photoadditions of aromatic compounds

McCullough¹

1987

Chem. Rev.

185

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“…See DOI: 10.1039/b000000x/ sive property in large polycyclic molecules. [14][15][16][17][18][19] An experimental technique to study molecular aromaticity is nuclear magnetic resonance (NMR) spectroscopy. 20,21 External magnetic fields induce current densities in molecules, which in turn induce weak secondary magnetic fields.…”

Section: Introductionmentioning

confidence: 99%

The influence of heteroatoms on the aromatic character and the current pathways of B₂N₂-dibenzo[a,e]pentalenes

Dimitrova

Fliegl

Sundholm

2017

Phys. Chem. Chem. Phys.

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Four polycyclic molecules have been investigated at the DFT B3LYP/def2-TZVP level of theory using calculated magnetically induced current densities as an indicator of their (anti)aromaticity. Complicated current pathways were found in dibenzo[a,e]pentalene and its three heterocyclic analogues each containing two boron and two nitrogen atoms. The antiaromatic character of the pentalene moiety is weaker in the hydrocarbon molecule and in 5,11-dihydrobenzo[d]benzo[4,5][1,2,3]azadiborolo[3,2-b][1,2,3]azadiborole as compared to the pentalene molecule. The antiaromatic character of the pentalene moiety is completely absent in the other two heterocyclic structures. In 6,12-dihydrobenzo[d]benzo[4,5][1,2,3]diazaborolo[2,1-a][1,2,3]diazaborole all four molecular rings are aromatic according to the ring-current criterion, and in 6,12-dihydrobenzo[d]benzo[3,4][1,2,5]azadiborolo[1,2-a][1,3,2]diazaborole, the diazaborole ring is aromatic, while the azadiborole ring is antiaromatic. In all four molecules the six-membered rings are aromatic sustaining a weaker ring current than benzene does.

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ChemInform Abstract: SYNTHESIS AND REACTIONS OF 5,6,11,12‐TETRAHYDRO‐5,12;6,11‐DIETHENODIBENZO(A,E)CYCLOOCTENE (PP′‐DINAPHTHALENE)

Tobe¹,

Hirata²,

Nishida³

et al. 1981

Chemischer Informationsdienst

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Synthesis and reactions of 5,6,11,12-tetrahydro-5,12;6,11-diethenodibenzo-[α,e]cyclo-octene (pp′-dinaphthalene)

Cited by 9 publications

References 0 publications

Photoadditions of aromatic compounds

Photoadditions of aromatic compounds

The influence of heteroatoms on the aromatic character and the current pathways of B₂N₂-dibenzo[a,e]pentalenes

ChemInform Abstract: SYNTHESIS AND REACTIONS OF 5,6,11,12‐TETRAHYDRO‐5,12;6,11‐DIETHENODIBENZO(A,E)CYCLOOCTENE (PP′‐DINAPHTHALENE)

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Synthesis and reactions of 5,6,11,12-tetrahydro-5,12;6,11-diethenodibenzo-[α,e]cyclo-octene (pp′-dinaphthalene)

Cited by 9 publications

References 0 publications

Photoadditions of aromatic compounds

Photoadditions of aromatic compounds

The influence of heteroatoms on the aromatic character and the current pathways of B2N2-dibenzo[a,e]pentalenes

ChemInform Abstract: SYNTHESIS AND REACTIONS OF 5,6,11,12‐TETRAHYDRO‐5,12;6,11‐DIETHENODIBENZO(A,E)CYCLOOCTENE (PP′‐DINAPHTHALENE)

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The influence of heteroatoms on the aromatic character and the current pathways of B₂N₂-dibenzo[a,e]pentalenes