Intermolecular free radical additions to strained cycloalkenes. Cyclopropene and cyclobutene as radical acceptors

Ferjancic, Zorana; Čeković, Živorad; Saičić, Radomir N.

doi:10.1016/s0040-4039(00)00286-0

Cited by 35 publications

(14 citation statements)

References 5 publications

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“…Radical reactions with cyclopropenes have been barely studied. Indeed, only a few reports on radical additions to the π-system of cyclopropenes with preservation of the ring were reported. − In 2015, Miyata and co-workers reported the addition of trichloromethyl radicals generated from chloroform ( 392 ) to cyclopropenes 391 bearing a methylene attached at C1 which occurred though unprecedented ring-opening reaction (Scheme ). Particularly, the authors found that when Me 2 Zn was employed as radical initiator, the reaction led to the formation of open-chain products 393 containing a 1,1-dichloroalkene group.…”

Section: Other C–c Bond Cleavage Reactions Of Cyclopropenesmentioning

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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Section: Other C–c Bond Cleavage Reactions Of Cyclopropenesmentioning

confidence: 99%

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

Vicente

2020

Chem. Rev.

139

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“…In 1994, the research group of Nakamura reported the cyclopropene radical hydrostannation . Later on, not only xanthate, bromine atom transfer processes were also reported by the researchers . Continuation of their interest in recent studies, Landais group described the visible light mediated addition of phenacyl bromides with cyclopropenes using iridium photocatalyst to rendered the naphthalenones with acceptable yields under conventional reaction conditions (Scheme ) …”

Section: Using Metal Catalysismentioning

confidence: 99%

Recent Developments in Radical‐Mediated Transformations of Organohalides

Lekkala

Balakrishna

et al. 2019

Eur J Org Chem

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In recent years, radical‐mediated transformations of organohalides, a class of powerful chemical transformations, have become an important field at the forefront of organic chemistry. Formation of free‐radicals from organohalides is among the most useful methods to access open‐shell reactive intermediates that have a number of established applications in chemical synthesis. Herein we summarize most of the strategies involving metal‐catalyzed, non‐metal‐catalyzed, as well as catalyst‐free radical‐mediated transformations of organohalides.

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“…Photochemically induced trans-selective addition of xanthanes to cyclopropenone acetal is another example of a rare type of reaction involving radical-initiated addition to cyclopropenes. 126,127 Thus, it was shown that cyclopropenone acetal 6 afforded the corresponding cyclopropyl dithiocarbonates 109 in moderate yields (Scheme 70). 126…”

Section: Scheme 69mentioning

confidence: 99%

“…126,127 Thus, it was shown that cyclopropenone acetal 6 afforded the corresponding cyclopropyl dithiocarbonates 109 in moderate yields (Scheme 70). 126…”

Section: Scheme 69mentioning

confidence: 99%