Photocycloadditions of tetrachloro-1,4-benzoquinone (chloranil) onto cyclobutene and cyclopropene. Expected and unexpected products

Braun, M.; Christl, Manfred

doi:10.1039/c2ob07048k

Cited by 5 publications

(2 citation statements)

References 34 publications

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“…421 The reaction of chloranil (220) with several olefins can be successfully conducted as a monoaddition reaction if the irradiation wavelength is properly chosen. Christl and co-workers 422,423 isolated the intermolecular [2 + 2] photocycloaddition product 221 of cyclooctene when visible light was employed for excitation (Scheme 69). Irradiation at a shorter wavelength led to multiple addition and other side reactions.…”

Section: -Cyclopentenonesmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: -Cyclopentenonesmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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“…A year later, Christl and co-workers described the photocycloaddition of cyclopropene (366) with chloranil (367) (Scheme 54B). 256 Irradiation at −30 °C of a benzene solution of the mixture with a medium-pressure Hg-lamp using adequate light filters to ensure light with wavelength (<400 nm), followed by replacing benzene by methanol (once 366 was consumed) led to the formation of tetracycle 368 as the single reaction product in 36% yield. This unexpected result indicated that two molecules of cyclopropene were incorporated to the product under photoexcitation, with one preserving the three-membered ring.…”

Section: Rearrangements Of Cyclopropenes Via C−c Bond Cleavagementioning

confidence: 99%

C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

Vicente

2020

Chem. Rev.

139

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This review highlights key reactivities relying on C–C bond cleavages of cyclopropenes. Metal-catalyzed and metal-free transformations are covered in reactions involving direct ring-opening processes or transformations through nonisolable cyclopropane intermediates generated from cyclopropenes. Special emphasis is on the synthetic utility and mechanistic aspects of methodologies discussed along the revision. Different types of reactivities are covered in separate sections including generation of vinyl carbenes and their reactions, metathesis processes, heterocycles syntheses, SEAr reactions, metalation-ring opening sequences, cycloadditions involving ring-cleavages or rearrangements. The focus is on results described from 2007 to the end of 2019, yet relevant pioneering transformations are eventually included.

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Cyclopropenes for the Synthesis of Cyclopropane‐Fused Dihydroquinolines and Benzazepines

et al. 2015

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An efficientm ethod for the construction of cyclopropane-fused dihydroquinolines was established by an ovel Povarov-type three-component reaction of aromatic aldehydes,a nilines and cyclopropenesi nt he presence of trifluoromethanesulfonic acid. Ther eactionp roceeded in ar egioselective and diastereoselective manner. Furthermore,t he dihy-droquinolines were smoothly converted to benzazepine derivatives via ar ing opening/isomerization sequence,furtherexpanding the synthetic scope. Results and DiscussionInitially,t he cycloaddition reactiono fb enzaldehyde (4a), aniline (5a), and cyclopropene (6a)w as chosen as the model reaction( Table1). Because of the adverse effect of water, the reactionw as carriedo ut in

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Photocycloadditions of tetrachloro-1,4-benzoquinone (chloranil) onto cyclobutene and cyclopropene. Expected and unexpected products

Cited by 5 publications

References 34 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

Cyclopropenes for the Synthesis of Cyclopropane‐Fused Dihydroquinolines and Benzazepines

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Photocycloadditions of tetrachloro-1,4-benzoquinone (chloranil) onto cyclobutene and cyclopropene. Expected and unexpected products

Cited by 5 publications

References 34 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

Cyclopropenes for the Synthesis of Cyclopropane‐Fused Dihydroquinolines and Benzazepines

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions