ChemInform Abstract: PHOTOREACTIVITY IN SOLUTION. PART 18. INTRAMOLECULAR PHOTOADDITION OF THE EXCITED CARBONYL GROUP OF CYCLOALKANONES TO A NONCONJUGATED ETHYLENIC DOUBLE BOND

Kossanyi, J.; Jost, P.; Furth, Bernard; Daccord, G.; Chaquin, Patrick

doi:10.1002/chin.198107132

Cited by 3 publications

(4 citation statements)

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“…Our findings resemble a report of Kossanyi et al concerning photoreactions of 2-allylcyclopentanone . The authors observed the formation of both crossed and straight oxetanes in nearly equal amounts.…”

Section: Resultssupporting

confidence: 92%

Photoinduced Electron Transfer Reactions of α-Cyclopropyl- and α-Epoxy Ketones. Tandem Fragmentation−Cyclization to Bi-, Tri-, and Spirocyclic Ketones

Kirschberg

Mattay

1996

J. Org. Chem.

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Reductive photoinduced electron transfer (PET) reactions have been performed with various bicyclic alpha-cyclopropyl-substituted ketones and tertiary amines. The reaction resulted in a regioselective cleavage of one cyclopropyl bond under formation of an exocyclic radical with an endocyclic enolate unit. In the case of bicyclic ketones with an unsaturated side chain, various bicyclic, spirocyclic, and tricyclic products are accessible via radical cyclization, depending on the position of the alkenyl substituent. In addition to triethylamine, N-silylated amines have also been used as electron donors, leading to a variety of compounds, among them are silylated fragmentation products, indicating that a proton is transferred from not only the amine radical cation but also the cationic silyl group. The intramolecular Paternó-Büchi reaction has also been studied for cyclopropane derivatives of the jasmone type leading to tetracyclic oxetanes. Finally, alpha-epoxy-substituted ketones have been investigated under PET conditions, yielding ring-opened products.

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Section: Resultssupporting

confidence: 92%

Photoinduced Electron Transfer Reactions of α-Cyclopropyl- and α-Epoxy Ketones. Tandem Fragmentation−Cyclization to Bi-, Tri-, and Spirocyclic Ketones

Kirschberg

Mattay

1996

J. Org. Chem.

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“…In contrast, if 7-Cy is used as reaction vessel, the alkyl carbene to a significant amount may also insert into the O-H bonds of the host, [18] a process that also explains the low recovery of products after irradiation of 1b@7-Cy. But since TRIMEB does not possess functional groups or bonds which are susceptible to react easily with a relatively nucleophilic alkyl carbene, [7] 1a only can rearrange intramolecularly, affording endo-tricyclo[3.3.0.0 2,8 ]octan-3-ol (7a) [19] and bicyclo[3.3.0]oct-5-en-3-ol (6a) [20] in a ratio depending on the host molecule used. In the case of 1a@TRIMEB, the larger size of the cavity also allows a total separation of one guest molecule from another.…”

Section: Discussionmentioning

confidence: 99%

Supramolecular Photochirogenesis with Carbenes Entrapped in Cyclodextrins

Mieusset¹,

Wagner²,

Su³

et al. 2009

Eur J Org Chem

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Two achiral diazirines 1a and 1b have been encapsulated in the inherently chiral cavity of α-cyclodextrin (6-Cy), β-cyclodextrin (7-Cy) and permethylated β-cyclodextrin (TRIMEB) and photolyzed. Because of supramolecular photochirogenesis the generated carbenes afford intramolecular C-H insertion products not as a racemate but one enantiomer is slightly favored. With 1a@(6-Cy) 2 the ee of product 7a is doubled. To the best of our knowledge for the first time for carbene

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“…An intramolecular reaction on allyl cyclopentanone derivatives has been reported [227,252,253]. In this case both straight 37 and crossed 38 oxetanes can be obtained (Scheme 43).…”

Section: Intramolecular Reactionsmentioning

confidence: 99%

“…The reaction of biacetyl with benzvalene gave the corresponding adduct, while benzophenone gave, as the only product, benzene [44]. When homobenzvalene was used as the alkene in the reaction with ethyl phenylglyoxylate, the irradiation gave the corresponding adduct in 70% yield with high stereoselectivity (Scheme 39) [227].…”

Section: Other Intermolecular Reactionsmentioning

confidence: 99%

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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ChemInform Abstract: PHOTOREACTIVITY IN SOLUTION. PART 18. INTRAMOLECULAR PHOTOADDITION OF THE EXCITED CARBONYL GROUP OF CYCLOALKANONES TO A NONCONJUGATED ETHYLENIC DOUBLE BOND

Abstract: Allylcycloalkanone wie (I) ergeben unter Lichteinwirkung hauptsächlich die Oxetane (II) und (III), wobei das Produktverhältnis (II)/(III) zwischen 2:1 und 1:4 liegt.

Cited by 3 publications

References 0 publications

Photoinduced Electron Transfer Reactions of α-Cyclopropyl- and α-Epoxy Ketones. Tandem Fragmentation−Cyclization to Bi-, Tri-, and Spirocyclic Ketones

Photoinduced Electron Transfer Reactions of α-Cyclopropyl- and α-Epoxy Ketones. Tandem Fragmentation−Cyclization to Bi-, Tri-, and Spirocyclic Ketones

Supramolecular Photochirogenesis with Carbenes Entrapped in Cyclodextrins

Oxetane Synthesis through the Paternò-Büchi Reaction

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