The synthesis of exo,exo-11-oxatetracyclo[4.4.1.0.2,507,10]undeca-3,8-diene. The stereochemistry of the tricyclo[6.2.0.03,6]decane derivative obtained by the photodimerisation of dimethyl trans,trans-penta-1,4-dien-3-one-1,5-dicarboxylate

Rowland, Neil E.; Sondheimer, Franz; Bullock, Graham; LeGoff, Eugene; Grohmann, K.

doi:10.1016/s0040-4039(00)89341-7

Cited by 6 publications

(1 citation statement)

References 9 publications

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“…14 It is postulated that remote ClNNNCl interactions (and/or p-interactions) assist CLC double bond alignment into a viable geometry for favourable cycloaddition. Structurally-related dba compounds, 15 such as conformationally restricted 2,5-dibenzylidenecyclopent-3-ene-1-one {the 1,4-dien-3-one moitey is locked in a s-cis,s-cis conformation, with non-parallel CLC double bonds (3.92 A ˚) between molecules, Scheme 1, reaction [b]} and penta-1,4-diene-3-one-1,5-dicarboxylate 16 have been reported to undergo [2+2] cycloaddition.…”

Section: Introductionmentioning

confidence: 99%

Photochemical-mediated solid-state [2+2]-cycloaddition reactions of an unsymmetrical dibenzylidene acetone (monothiophos-dba)

et al. 2012

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A novel unsymmetrical dibenzylidene acetone (monothiophos-dba, compound 3), containing two chemically different alkene moieties, undergoes a selective photochemically-induced [2+2] cycloaddition solid-state transformation (single crystal and powder), as shown by X-ray diffraction methods. In the single crystal the rate constant for the cycloaddition reaction was determined {k = (2.3 ¡ 0.1) 6 10 24 s 21 }, with a 69% conversion attained, which compares well with a twophoton irradiation experiment using a Nd:YAG laser pumped dye laser at 605 nm radiation (66% conversion). Full conversion was attained using powdered 3 after 43 h. A similar conversion was noted between the single crystal and powder forms (59% and 66% conversion after 5 h irradiation). Irradiation of monothiophos-dba in solution using a 325 nm laser, and monitoring by 1 H NMR spectroscopy, showed that no cycloaddition occurred, but exclusive photochemically-induced trans A cis isomerisation of the alkene bond connecting the unsubstituted aryl group (cis A trans isomerisation in these electron-deficient and polarised CLC bonds occurs rapidly by thermal equilibration).

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Section: Introductionmentioning

confidence: 99%

Photochemical-mediated solid-state [2+2]-cycloaddition reactions of an unsymmetrical dibenzylidene acetone (monothiophos-dba)

et al. 2012

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Light‐Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π‐Expanded Imidazoles

Skonieczny

Gryko

2016

Chemistry An Asian Journal

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π-Expanded imidazoles bearing the 2-iodophenyl substituent at position 2 undergo direct photoinduced intramolecular arylation in the solid, crystalline state leading to large non-planar heterocycles. An analogous reaction employing 2-bromophenyl and 2-chlorophenyl substituents is considerably slower. Such processes have never before been demonstrated to occur in crystals and have allowed the efficient synthesizes of structurally unique compounds containing either the phenanthro[9',10':4,5]imidazo[1,2-f]phenanthridine moiety or structurally related skeletons. The reaction occurs in the thin crystalline layers irradiated with UV photons in an almost quantitative manner over 48-72 h. Several previously unknown architectures have been prepared using this methodology. Furthermore, the optical properties of these π-expanded imidazoles can be altered with the addition of heteroatoms and/or electron-donating groups.

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ChemInform Abstract: DIE SYNTHESE VON EXO,EXO‐11‐OXA‐TETRACYCLO(4,4,1,0(2,5),0(7,10))UNDECA‐3,8‐DIEN, DIE STEREOCHEMIE VON TRICYCLO(6,2,0,0(3,6))‐DERIVATEN AUS DER PHOTODIMERISIERUNG VON TRANS,TRANS‐PENTA‐1,4‐DIEN‐3‐ON‐1,5‐DICARBONSAEUREDIMETHYLESTER (I)

Rowland¹,

Sondheimer²,

Bullock³

et al. 1971

Chemischer Informationsdienst. Organische Chemie

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The synthesis of exo,exo-11-oxatetracyclo[4.4.1.0.2,507,10]undeca-3,8-diene. The stereochemistry of the tricyclo[6.2.0.03,6]decane derivative obtained by the photodimerisation of dimethyl trans,trans-penta-1,4-dien-3-one-1,5-dicarboxylate

Cited by 6 publications

References 9 publications

Photochemical-mediated solid-state [2+2]-cycloaddition reactions of an unsymmetrical dibenzylidene acetone (monothiophos-dba)

Photochemical-mediated solid-state [2+2]-cycloaddition reactions of an unsymmetrical dibenzylidene acetone (monothiophos-dba)

Light‐Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π‐Expanded Imidazoles

ChemInform Abstract: DIE SYNTHESE VON EXO,EXO‐11‐OXA‐TETRACYCLO(4,4,1,0(2,5),0(7,10))UNDECA‐3,8‐DIEN, DIE STEREOCHEMIE VON TRICYCLO(6,2,0,0(3,6))‐DERIVATEN AUS DER PHOTODIMERISIERUNG VON TRANS,TRANS‐PENTA‐1,4‐DIEN‐3‐ON‐1,5‐DICARBONSAEUREDIMETHYLESTER (I)

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