Radical ions and photochemical charge transfer phenomena Part 32. Cyclobutane and cyclopropane ring opening reactions by photoinduced electron transfer - a new ring expansion method

Bischof, Eric W.; Mattay, Jochen

doi:10.1016/1010-6030(92)85143-i

Cited by 18 publications

(1 citation statement)

References 9 publications

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“…Identical results were obtained by treatment with Zn in methanol in the presence of zinc chloride . Quite gratifyingly, however, the reductive photoinduced electron transfer ( h ν 254 nm, Et 3 N, LiClO 4 , CH 3 CN) provided the methylcyclopentanone 6ab in 60% yield. An even better yield was obtained by reductive cleavage using samarium iodide, which afforded 6ab in 74% yield.…”

supporting

confidence: 52%

Intermolecular Pauson−Khand Reactions of Cyclopropene: A General Synthesis of Cyclopentanones

Marchueta¹,

Moyano²,

Pericàs³

et al. 2001

Org. Lett.

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[reaction: see text] The Pauson-Khand reaction of cyclopropene with a variety of terminal alkynes has been studied. The best reaction conditions involve NMO activation in CH(2)Cl(2) at -35 degrees C. In this way, 3-substituted-bicyclo[3.1.0]hex-3-en-2-ones have been obtained in good to excellent yields. As a synthetic application, several types of substituted cyclopentenones have been prepared from these cycloadducts by protocols involving conjugate addition and reductive ring opening.

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supporting

confidence: 52%

Intermolecular Pauson−Khand Reactions of Cyclopropene: A General Synthesis of Cyclopentanones

Marchueta¹,

Moyano²,

Pericàs³

et al. 2001

Org. Lett.

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Electron‐transfer Reactions of Amines

Das¹,

Suresh²

2001

Electron Transfer in Chemistry

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Photoreactions of Enones with Amines – Cyclization of Unsaturated Enones and Reductive Ring Opening by Photoinduced Electron Transfer (PET)

et al. 1992

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Photolysis of the unsaturated enones 1 yields [2 + 21 cycloaddition products 2 and 3 with varying regioselectivity. Under electron-transfer conditions (PET) spirocyclic products 4 are formed. The straight [2 + 2 1 cycloaddition products 2b.c.f are converted to the spirocyclic products 4b,c,f under the same reaction conditions. The cyclobutane 5 and the cyclopropane 11 also undergo this new reductive ring opening reaction, while the stabilized system 7 is converted to reduced ringenlarged triquinane 10 which may be interesting in natural product synthesis. -Irradiation of 2-cyclohexen-1-one (14) in the presence of N,N-dimethylallylamine (15) leads to the decahydroisoquinoline 18. A mechanism involving radical intermediates is discussed. On the other hand, radical reactions have been used for reductive ring opening processes of strained systems[91 leading yields We to now new medium-sized report spirocyclic on the rings. compounds["', cyclization of olefinic and on enones, the reductive which % % % ring opening of strained systems, both induced by photoinduced electron transfer (PET). Chem. Unsaturated Enones

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Radical ions and photochemical charge transfer phenomena Part 32. Cyclobutane and cyclopropane ring opening reactions by photoinduced electron transfer - a new ring expansion method

Cited by 18 publications

References 9 publications

Intermolecular Pauson−Khand Reactions of Cyclopropene: A General Synthesis of Cyclopentanones

Intermolecular Pauson−Khand Reactions of Cyclopropene: A General Synthesis of Cyclopentanones

Electron‐transfer Reactions of Amines

Photoreactions of Enones with Amines – Cyclization of Unsaturated Enones and Reductive Ring Opening by Photoinduced Electron Transfer (PET)

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