Spiroconjugation

Simmons, Howard E.; Fukunaga, Tadamichi

doi:10.1021/ja00996a022

Cited by 310 publications

(171 citation statements)

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“…Structure in the crystal and numbering scheme of 48. [11] 248 (2) [9] A suspension of 1.00 g (6.2 mmol) of indantrione (19), 0.51 mL (7.2 mmol) of 2-bromoethanol The structure confirms the NOE results and is the proof and 3 mL of THF is mixed with 1.00 g (7.2 mmol) of potassium that the diene in these reactions attacks from the face of carbonate and 3 mL of DMSO. After 24 h at 40°C the yellowthe ligand opposite to the tricarbonylchromium group.…”

Section: 3-bis(ethylenedioxy)-2-indanone (18)mentioning

confidence: 53%

“…yellow powder (m. p. 138°C), which was identified spectroscopiThe successful hetero-DielsϪAlder reactions starting cally. [9,10] from ninhydrin complex 8 show that this compound may 1,2,3-Tris(ethylenedioxy)indane (16): a) 4.00 g (19.6 mmol) of 20, be used as a substitute of the dehydrated indantrione com-6.90 g (6.2 mL, 111.1 mmol) of 1,2-ethanediol, and 15 mg (0.1 plex 7. We currently investigate reactions of 8 and related mmol) of PTSA in 100 mL of benzene is heated at reflux with complexes in more depth with some emphasis on addition azeotropic water removal.…”

Section: 3-bis(ethylenedioxy)-2-indanone (18)mentioning

confidence: 99%

“…[1] While the acetalization under standard conditions took place only at the keto groups adjacent to the aromatic ring, As with benzocyclobutenedione, all attempts to directly selective acetalization was possible at C-2 using 2-bromocoordinate the ligands by treatment of indantrione (19) or ethanol/potassium carbonate. [9] Starting from ninhydrin ninhydrin (17) with hexacarbonylchromium or triammine-(17) or indantrione (19) the sequence of acetalization reactricarbonylchromium were not successful and resulted in tions is interchangeable, so that either 18 or 20 are interdecomposed material only. A retrosynthetic analysis of the problem led to five different possible ways to 7 or 8 starting from 9Ϫ12 and 6.…”

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confidence: 99%

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Synthesis, Characterization, and Some Reactions of the Tricarbonylchromium Complexes of 1,3-Indandione and Ninhydrin

Leinweber

Wartchow

Butenschön³

1999

Eur. J. Org. Chem.

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The syntheses and characterization of the tricarbonylchromium complexes of 1,3‐indandione and ninhydrin are described. As the direct complexation proved unsuccessful, the acetal route was tried. Although some complexes were obtained, complex deacetalization did not work in the case of ninhydrin. Finally, the oxidation of tricarbonyl(η6‐1,3‐indandione)chromium(0) with dimethyldioxirane gave the ninhydrin complex in 75% yield in equilibrium with the indantrione complex. The latter reacts in hetero Diels‐Alder reactions with dienes with diastereoselective formation of spiro anellated pyran derivatives.

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Section: 3-bis(ethylenedioxy)-2-indanone (18)mentioning

confidence: 53%

Section: 3-bis(ethylenedioxy)-2-indanone (18)mentioning

confidence: 99%

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confidence: 99%

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Synthesis, Characterization, and Some Reactions of the Tricarbonylchromium Complexes of 1,3-Indandione and Ninhydrin

Leinweber

Wartchow

Butenschön³

1999

Eur. J. Org. Chem.

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“…Therefore, the energy gap between the two NBMOs ψ S,OR and ψ A,OR becomes large enough for the singlet ground state. The notable effect of the cyclic acetal group arises because of the spiroconjugation 20 of ψ A with n O (Figure 5b), which is an additional interaction to the hyperconjugative interaction of ψ S with σ* CO . The spiroconjugation destabilizes ψ A to increase the energy gap between ψ S,OR and ψ A,OR , leading to a larger energy spacing in CP1e compared with those in CP1b and CP1d.…”

Section: ¹1mentioning

confidence: 99%

Is π-Single Bonding (C–π–C) Possible? A Challenge in Organic Chemistry

Abe

Akisaka

2017

Chem. Lett.

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Rikuo Akisaka received his Bachelor's degree in 2016 from University of Tsukuba. He is currently a master's program student at the department of chemistry, graduate school of science, Hiroshima University, under the supervision of professor Manabu Abe. His current research focuses on steric effect on the reactivity of singlet 2,2-dialkoxy-1,3-diyls. AbstractChemical bonding systems determine the nature of molecules. In organic chemistry, there are two bonding types for carbon carbon connections: σ-bonding and π-bonding. In this Highlight Review, several aspects of studies in the last two decades addressing a naive question "Is π-single bonding (CπC) possible?" were reviewed: (1) features of π-single bonded species; (2) molecular design for π-single bonding; (3) generation and detection of singlet diradicaloids with a π-single bonding character; (4) future prospects of π-single bonded species.

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“…Spiro compounds have also been of great interest in the development of the theory of spiroconjugation (Simmons & Fukunaga, 1967;Boschi, Dreiding & Heilbronner, 1970) as well as extending the theory of energy transfer between intramolecular chromophores (Keller, 1968;Hudson & Hedges, 1969).…”

Section: Introductionmentioning

confidence: 99%

Structure solution by visual packing and optimization techniques. The crystal and molecular structure of spiro[5,5]undeca-1,4,7,10-tetraene-3,9-dione

Cullen¹,

Hass²,

Klunk³

et al. 1976

Acta Crystallogr Sect B

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The structure of spiro [5,5]undeca-l,4,7,10-tetraene-3,9-dione, C~IHsO2, has been determined from three-dimensional X-ray counter data. The crystals have the space group P]" with a= 9.080 (4), b= 13.608 (2), c=7.493 (3)/~, a=91"11 (2), fl=96-91 (4), y= 100.50 (2) ° and four molecules per unit cell. The observed and calculated densities are 1.26 (1) and 1.272 g cm -a respectively. 3180 independent reflections were collected by the 0=20 scan method. The structure was solved independently by two methods. In one method a three-dimensional color television display system was used to search for the most likely packing arrangements in the unit cell. The other method involved an application of Boolean programming. Both methods arrived at the same model, which was refined by least-squares techniques to a conventional R index of 0"048 for the 1485 reflections having I>_ 3at. The two independent molecules in the asymmetric unit are virtually identical and consist of two cyclodienone rings joined by a common spiro C atom. The average C-C bond length for bonds involving the spiro C atom is 1"50 (1)/~. The average bond angle around this atom is 109"4 ° .

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Spiroconjugation

Cited by 310 publications

References 2 publications

Synthesis, Characterization, and Some Reactions of the Tricarbonylchromium Complexes of 1,3-Indandione and Ninhydrin

Synthesis, Characterization, and Some Reactions of the Tricarbonylchromium Complexes of 1,3-Indandione and Ninhydrin

Is π-Single Bonding (C–π–C) Possible? A Challenge in Organic Chemistry

Structure solution by visual packing and optimization techniques. The crystal and molecular structure of spiro[5,5]undeca-1,4,7,10-tetraene-3,9-dione

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