Intramolecular [3+2]-photocycloadditions of alkenyl methyl 1,4-naphthalenedicarboxylates

Kubo, Yasuo; Adachi, Tsubasa; Miyahara, Nana; Nakajima, Satoshi; Inamura, Isamu

doi:10.1016/s0040-4039(98)02149-2

Cited by 6 publications

(2 citation statements)

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“…The 1,8-mode of [3+2]-photocycloaddition of alkenes to the naphthalene ring, as reported for naphthalene-1,4-dicarboxylic acid diesters, 25,26 has not been observed so far for α-cyanoenamines and related captodative alkenes. From all of this, it has been demonstrated that photocycloadditions of captodative alkenes, especially α-cyanoenamines, to 1-acyl-naphthalenes (acyl = CHO, COCH 3 , COPh, COOCH 3 ) and analogues thereof are governed by the following selectivities: 1.…”

Section: Methodsmentioning

confidence: 87%

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Döpp¹,

Kruse²,

Erian³

et al. 2013

Arkivoc

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2-(Cycloamino)propenenitriles H 2 C=C(CN)N(CH 2 ) n (n = 4, 5, 6, 7) are added to triplet π,π*-excited 1-acetonaphthone forming 8b-acetyl-2-(cycloamino)-1,2,2a,8b-tetrahydrocyclobuta-[a]naphthalene-2-carbonitriles as well as 1-acetyl-9-(cycloamino)-1,4-dihydro-1,4-ethanonaphthalene-9-carbonitriles. Regio-and stereoselectivity of the photocycloadditions and the special role of the cyclobuta[a]naphthalene adducts in the initial stage of the photoadditions are discussed.

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Section: Methodsmentioning

confidence: 87%

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Döpp¹,

Kruse²,

Erian³

et al. 2013

Arkivoc

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“…The reaction at the 1,4‐position (photo‐Diels‐Alder reaction) proceeds stepwise mainly via excited triplet state [33,40,44,52,56,60,65,70,71,75–80] . In the reaction at the 1,8‐position, tetrahydroacenaphthylene derivatives are obtained via the formation of zwitter ion and subsequent proton transfer [45,73,81–85] . Mixtures of compounds with different reaction modes are obtained in many photoreactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐Oxatricyclo[7.2.0.0^1,5]undeca‐7,10‐dienes through Intramolecular Photocycloaddition Reactions of Alkenes to 1,8 a‐Position of Naphthalene Ring

et al. 2022

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Benzene solutions of 1-(5-aryl-2-oxapent-4-enyl)-2-cyanonaphthalenes 6 were irradiated with a high-pressure mercury lamp for 20 h to give 3-oxatricyclo[7.2.0.0 1,5 ]undecadienes 7 in good yields. In all cases, the trans isomer was preferentially obtained. Sensitization and quenching experiments showed that the reaction proceeds via an excited singlet state. When a dichloromethane solution of 6 was irradiated for only 1 h, an eightmembered ring compound 8 was obtained as an intermediate. When the obtained 8 was irradiated, the final product 7 was produced. The long wavelength absorption of 6 originates from the 2-cyanonaphthalene chromophore, indicating that the reaction is initiated by photoexcitation of the naphthalene ring. In addition, the fluorescence of 6 was intramolecularly quenched, and a weak intramolecular exciplex emission was observed at 400-550 nm. In this reaction, after photoexcitation of 6, a [2 + 2] photocycloadduct is formed at the 1,8a-position of the naphthalene ring via an intramolecular singlet exciplex, followed by thermal ring-opening and 4π disrotatory ringclosure leads to 7.

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ChemInform Abstract: Intramolecular [3 + 2]‐Photocycloadditions of Alkenyl Methyl 1,4‐Naphthalenedicarboxylates.

et al. 1999

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Intramolecular [3+2]-photocycloadditions of alkenyl methyl 1,4-naphthalenedicarboxylates

Cited by 6 publications

References 10 publications

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Synthesis of 3‐Oxatricyclo[7.2.0.0^1,5]undeca‐7,10‐dienes through Intramolecular Photocycloaddition Reactions of Alkenes to 1,8 a‐Position of Naphthalene Ring

ChemInform Abstract: Intramolecular [3 + 2]‐Photocycloadditions of Alkenyl Methyl 1,4‐Naphthalenedicarboxylates.

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Intramolecular [3+2]-photocycloadditions of alkenyl methyl 1,4-naphthalenedicarboxylates

Cited by 6 publications

References 10 publications

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Synthesis of 3‐Oxatricyclo[7.2.0.01,5]undeca‐7,10‐dienes through Intramolecular Photocycloaddition Reactions of Alkenes to 1,8 a‐Position of Naphthalene Ring

ChemInform Abstract: Intramolecular [3 + 2]‐Photocycloadditions of Alkenyl Methyl 1,4‐Naphthalenedicarboxylates.

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Synthesis of 3‐Oxatricyclo[7.2.0.0^1,5]undeca‐7,10‐dienes through Intramolecular Photocycloaddition Reactions of Alkenes to 1,8 a‐Position of Naphthalene Ring