Small ring compounds—XLI

Fadel, Antoine; Salaün, Jacques; Conia, J. M.

doi:10.1016/s0040-4020(01)88564-1

Cited by 19 publications

(4 citation statements)

References 71 publications

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“…16) Even if [2.2.0]hexan-2-one 9 (n=0) was formed, reversibility of ketene cycloaddition 1) would lead to the more stable bridged regioisomer 10 (n=0).…”

Section: Resultsmentioning

confidence: 99%

Intramolecular [2+2] Cycloaddition of Homoallylketenes to Bicyclo[2.1.1]hexan-5-ones

et al. 2012

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“…16) Even if [2.2.0]hexan-2-one 9 (n=0) was formed, reversibility of ketene cycloaddition 1) would lead to the more stable bridged regioisomer 10 (n=0).…”

Section: Resultsmentioning

confidence: 99%

Intramolecular [2+2] Cycloaddition of Homoallylketenes to Bicyclo[2.1.1]hexan-5-ones

et al. 2012

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“…A Ru‐catalyzed photoinduced reductive mono‐debromination reaction was found by Reiser group, in methanolic water solvent (Scheme B). Similarly, several mono‐dehalogenation reactions were developed in ionic liquids, acidic medium and Zn/AcOH medium to furnish the selective mono‐halogenated products 66 – 68 (Schemes C–E). This reactivity is unique to α,α‐dihalocarbonyls.…”

Section: αα‐Dihaloketones As Building Blocks In Organic Synthesismentioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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“…In a search of a convenient source of cyclobutene, we have found that cyclobutyl tosylate can provide cyclobutene (8) free of its isomeric impurities in good yields. 6 The addition of dibromocarbene generated from CHBr 3 and KOt-Bu to cyclobutene (8) at -30 o C produced adducts 9, 10, and 11 in a ratio of 1:4:8, respectively (Scheme 2).…”

Section: Journal Of Chemical Research 2004mentioning

confidence: 99%

Addition of Dibromocarbene to Cyclobutene: Characterisation and Mechanism of Formation of the Products

Algı

Hökelek

Balcı

2004

Journal of Chemical Research

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Small ring compounds—XLI

Cited by 19 publications

References 71 publications

Intramolecular [2+2] Cycloaddition of Homoallylketenes to Bicyclo[2.1.1]hexan-5-ones

Intramolecular [2+2] Cycloaddition of Homoallylketenes to Bicyclo[2.1.1]hexan-5-ones

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Addition of Dibromocarbene to Cyclobutene: Characterisation and Mechanism of Formation of the Products

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