Ring‐Rearrangement Metathesis of Nitroso Diels–Alder Cycloadducts

Vincent, Guillaume; Kouklovsky, Cyrille

doi:10.1002/chem.201002558

Cited by 27 publications

(6 citation statements)

References 81 publications

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“…The simplest one is the vinyl nitrosocarbonyl 1f (Table , entry 6) generated in the presence of sodium periodate in methanol/water solution at 0 °C trapped with cyclopentadiene to give the corresponding HDA cycloadduct 34f in 72%yield (Scheme ). , …”

Section: Nitrosocarbonyl Generation Methodsmentioning

confidence: 99%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

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The nitrosocarbonyls (R-CONO) are highly reactive species and remarkable intermediates toward different synthetic targets. This review will cover a research area whose impact in current organic synthesis is constantly increasing in the chemical community. This review represents the first and comprehensive picture on the generation and trapping of nitrosocarbonyls and is solidly built on more than 380 papers. Six different classes of key starting materials such as hydroxamic acids, N-hydroxy carbamates, N-hydroxyureas, nitrile oxides, and 1,2,4-oxadiazole-4-oxides were highlighted. The content of the review surveys all the methods to generate the nitrosocarbonyls through different approaches (oxidative, thermal, photochemical, catalytic, aerobic, and the less common ones) in the light of efficiency, yields, and mildness. The most successful trapping agents employed to catch these fleeting intermediates are reviewed, exploiting their superior dienophilic, enophilic, and electrophilic power. The work is completed by paragraphs dedicated to the detection of the intermediates, theoretical studies, and insights about the challenges and future directions for the field.

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Section: Nitrosocarbonyl Generation Methodsmentioning

confidence: 99%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

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“…However, the beneficial presence of ethylene has been observed in several cases, where the initial ring opening upon ethenolysis produced linear terminal olefins that were prone to interact in an intramolecular mode with the pendant olefin to form new cyclic products ,. In some cases, the presence of ethylene also reduced the formation of polymeric materials through ring‐opening metathesis polymerization . Some examples of rearrangement of norbornene and oxanorbornene derivatives into fused bicyclic and tricyclic products are given in Scheme .…”

Section: Applications In Fine Chemistrymentioning

confidence: 99%

Ethenolysis: A Green Catalytic Tool to Cleave Carbon–Carbon Double Bonds

Bidange

Fischmeister

Bruneau

2016

Chemistry A European J

120

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Remarkable innovations have been made in the field of olefin metathesis due to the design and preparation of new catalysts. Ethenolysis, which is cross-metathesis with ethylene, represents one catalytic transformation that has been used with the purpose of cleaving internal carbon-carbon double bonds. The objectives were either the ring opening of cyclic olefins to produce dienes or the shortening of unsaturated hydrocarbon chains to degrade polymers or generate valuable shorter terminal olefins in a controlled manner. This Review summarizes several aspects of this reaction: the catalysts, their degradation in the presence of ethylene, some parameters driving their productivity, the side reactions, and the applications of ethenolysis in organic synthesis and in potential industrial applications.

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“…Kouklovsky and Vincent have disclosed the RRM of nitroso Diels–Alder (NDA) adducts with a variety of alkenes under microwave or conventional heating conditions by employing catalyst 2 or catalyst 5 to generate various bicyclic compounds [ 61 ]. In this regard, compound 287 was subjected to a RRM cascade by employing catalyst 2 in the presence of but-3-en-1-ol ( 288 ) under optimized reaction conditions (MW, toluene, 80 °C) and the expected tandem metathesis product 289b was obtained along with the ROM–RCM product 289a .…”

Section: Reviewmentioning

confidence: 99%

Recent applications of ring-rearrangement metathesis in organic synthesis

Kotha¹,

Meshram²,

Khedkar³

et al. 2015

Beilstein J. Org. Chem.

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SummaryRing-rearrangement metathesis (RRM) involves multiple metathesis processes such as ring-opening metathesis (ROM)/ring-closing metathesis (RCM) in a one-pot operation to generate complex targets. RRM delivers complex frameworks that are difficult to assemble by conventional methods. The noteworthy point about this type of protocol is multi-bond formation and it is an atom economic process. In this review, we have covered literature that appeared during the last seven years (2008–2014).

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Ring‐Rearrangement Metathesis of Nitroso Diels–Alder Cycloadducts

Cited by 27 publications

References 81 publications

Generation and Trapping of Nitrosocarbonyl Intermediates

Generation and Trapping of Nitrosocarbonyl Intermediates

Ethenolysis: A Green Catalytic Tool to Cleave Carbon–Carbon Double Bonds

Recent applications of ring-rearrangement metathesis in organic synthesis

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