The Photochemistry of Dienes and Polyenes: Application to the Synthesis of Complex Molecules

Nuss, John M.; West, F. G.

doi:10.1002/0470857218.ch7

Cited by 3 publications

(11 citation statements)

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“…The 2‐pyrone and furan units of secondary photoproduct underwent intramolecular [4 + 4]‐photocycloaddition for the generation of lactone bridged cyclooctadiene. This was confirmed when 2‐pyrone rearrangement products were irradiated to afford lactone bridged cyclooctadiene as major photoproducts .…”

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 67%

“…The formation of three new C─C bonds and the complete diastereoselectivity were attractive features of this compact [4 + 3]‐cycloaddition transition state with approach from the face opposite the epoxide. However, because of the competing solvent trapping, [2 + 2]‐photodimerization, and rearrangement, the generality of intermolecular reaction was limited (Scheme ).…”

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

“…This report has shown that only head‐to‐head product was produced with high exo face selectivity. Subsequently, this reaction was systematically explored by many groups, owing largely to the many pathways in which the 2,7‐dioxabicyclo[3.2.0]hept‐3‐ene ring system can be exploited (Scheme ).…”

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

“…An acetaldehyde was produced from unexpected product arising from a Norrish Type II cleavage of 4‐methylpentanal and subsequently cycloaddition of acetaldehyde with furan. The furan was formed from desired cycloadduct uneventfully via acid‐catalyzed aromatization and oxidation .…”

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

“…Adducts were afforded in low selectivity when (−)‐8‐phenylmenthyl and chiral glyoxylate derivative were irradiated. This is because of lack of exo or endo selectivity during photocycloaddition or to a bad ratio of s‐trans and s‐cis conformers (Scheme ).…”

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

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Synthesis of Three‐Membered and Four‐Membered Heterocycles with the Assistance of Photochemical Reactions

Kaur

2019

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Some transformations are not possible with ground-state reactions even in the presence of a catalyst; hence, they are performed under photochemical conditions. Electron transfer occurred even with the photochemical excitement of one molecule where redox reaction is not possible at the ground state. The side products were obtained from ground-state reactions. For C─C bond formation during photochemical reactions, there was no requirement of any chemical activation of the substrates. Therefore, these reactions are presented here for the synthesis of three-membered and four-membered heterocycles in the context of sustainable processes.

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Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 67%

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

Section: Photochemical‐assisted Synthesis Of Three‐membered and Four‐mentioning

confidence: 99%

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Synthesis of Three‐Membered and Four‐Membered Heterocycles with the Assistance of Photochemical Reactions

Kaur

2019

Journal of Heterocyclic Chem

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Lithium Hydroxide AssistedEndo‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones

Turnbull

McDonald

et al. 2021

Eur J Org Chem

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3-Acyl-4-hydroxypyan-2-ones with pendent furans, readily available from dehydroacetic acid, are substrates for intramolecular [4 + 4]-photocycloaddition. In the presence of stoichiometric lithium base, these substrates undergo conversion to lactone-bridged cyclooctenones in moderate to good yields upon irradiation in THF at 0°C. In contrast to other crossed [4 + 4]photocycloadditions of pyran-2-ones, these examples proceed with complete diastereoselectivity for the endo cycloadducts.

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Synthesis, Photochemistry, and Photophysics of Butadiene Derivatives: Influence of the Methyl Group on the Molecular Structure and Photoinduced Behavior

et al. 2011

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Novel butadiene derivatives display diverse photochemistry and photophysics. Excitation of 2-methyl-1-(o-vinylphenyl)-4-phenylbutadiene leads to the dihydronaphthalene derivative, whereas photolysis of the corresponding model o-methyl analogue results in the formation of the naphthalene-like derivative, deviating from the nonmethylated analogue of the prior starting compound and producing benzobi- and -tricyclic compounds. The effect of the methyl substituents is even more dramatic in the case of the dibutadienes. The parent unsubstituted compound undergoes photoinduced intramolecular cycloaddition giving benzobicyclo[3.2.1]octadiene, whereas the photochemical reaction of the corresponding dimethylated derivative shows only geometrical isomerization due to the steric effect of the substituents. Methyl groups on the butadiene backbones reduce the extent of conjugation, causing a blue-shift of the characteristic absorption band. The fluorescence efficiency is dramatically decreased, as a consequence of nonplanarity and reduced rigidity of the molecules due to the crowding by the methyl and phenyl groups together. Four molecules of very similar structures show dramatically different photoinduced behavior, revealing how changes of the nature and position of the substituents are valuable in understanding the photophysics and photochemistry of these types of compounds.

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The Photochemistry of Dienes and Polyenes: Application to the Synthesis of Complex Molecules

Cited by 3 publications

References 0 publications

Synthesis of Three‐Membered and Four‐Membered Heterocycles with the Assistance of Photochemical Reactions

Synthesis of Three‐Membered and Four‐Membered Heterocycles with the Assistance of Photochemical Reactions

Lithium Hydroxide AssistedEndo‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones

Synthesis, Photochemistry, and Photophysics of Butadiene Derivatives: Influence of the Methyl Group on the Molecular Structure and Photoinduced Behavior

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