Regio- and stereoselective photocycloadditions of heterocyclic 2,3-diones — Evidence for an unexpected 1,2-aroyl migration

Kollenz, G.; Terpetschnig, Ewald; Sterk, H.; Peters, Karl; Peters, E.‐M.

doi:10.1016/s0040-4020(99)00078-2

Cited by 18 publications

(10 citation statements)

References 54 publications

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“…The same behavior has been observed in the reaction between quinone and quadricyclane and norbornadiene [234,235]. The adduct was found also in the reaction between quinones and acenaphthylene [77]. Benzophenone can react also with a paracyclophane derivative 32 (Scheme 41) [54].…”

Section: Other Intermolecular Reactionssupporting

confidence: 60%

“…High regio- and stereoselectivity ( syn addition) was observed in the reaction of pentafluorobenzaldehyde with enol acetates [76]. The reaction between a 2,3-thiophenone derivative and vinyl acetate gave the corresponding adduct on a ketonic function in low yields [77]. The reaction between benzaldehyde and a silyl derivative of cinnamyl alcohol gave the corresponding oxetane with high stereoselectivity (Scheme 11) [78].…”

Section: Reactions With Electron Rich Unsaturated Compoundsmentioning

confidence: 99%

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Oxetane Synthesis through the Paternò-Büchi Reaction

D’Auria

Racioppi

2013

Molecules

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Abstract:The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds.

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Section: Other Intermolecular Reactionssupporting

confidence: 60%

Section: Reactions With Electron Rich Unsaturated Compoundsmentioning

confidence: 99%

Oxetane Synthesis through the Paternò-Büchi Reaction

D’Auria

Racioppi

2013

Molecules

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“…This example showed the formation of oxetanes by photochemical cycloaddition of carbonyl compounds to olefins (Scheme ).…”

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

confidence: 99%

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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“…2,3‐Furandiones (Fig. ) are very susceptible to attacking of nucleophiles and are very important synthon materials for lots of heterocyclic compounds [1], one of which is pyrazole derivatives.…”

Section: Introductionmentioning

confidence: 99%