Counterattack reagents in organic synthesis: versatility and efficiency

Hwu, Jih Ru; Tsay, Shwu‐Chen

doi:10.1039/a705054b

Cited by 13 publications

(5 citation statements)

References 33 publications

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“…Functioning as a “counterattack reagent”, , hexamethyldisilane can be used to bring about various organic functional group transformations. Examples include the conversion of allylic alcohols to allyltrimethylsilanes, conversion of hydrazines to 2-tetrazenes, polysilylation of hydrazines, and oxidation of benzyl alcohols to phenones or benzaldehyde .…”

Section: Introductionmentioning

confidence: 99%

Mono-deoxygenation of Nitroalkanes, Nitrones, and HeterocyclicN-Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent”

et al. 1999

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Transformation of secondary nitroalkanes to ketoximes was achieved in 40−73% yields by treatment of the corresponding nitronate anions with hexamethyldisilane. In this new mono-deoxygenation process, hexamethyldisilane acted as a “counterattack reagent”. The conversion of nitrones to imines was also achieved in 82−88% yields by use of trimethylsilyllithium. Similarly, heterocyclic N-oxides were converted to the corresponding N-heterocycles in 73−86% yields. These deoxygenation processes presumably involve a 1,2-elimination.

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Section: Introductionmentioning

confidence: 99%

Mono-deoxygenation of Nitroalkanes, Nitrones, and HeterocyclicN-Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent”

et al. 1999

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“…The "counterattack strategy" 25,26 adopted by our laboratory permits facile conversions of nitroalkanes or nitroalkenes to thiohydroxamic acids, thiohydroximates, nitriles, and oximes. Counterattack method exploits inherent reactivity of reagents.…”

Section: Conversions Of Nitro Compounds To Thiohydroxamic Acids Thiohydroximates Nitriles and Oximesmentioning

confidence: 99%

Recent Developments of Compounds Containing the Nitrogen-Oxygen Moiety in Organic Synthesis

Tsay¹,

Patel²,

Hwu³

1998

Synlett

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Moreover, α,β-unsaturated nitroalkenes can function as Michael acceptors to undergo a 1,2-or 1,4-addition reaction. We used these properties to synthesize allylic nitro compounds 8,9 from primary and secondary nitroalkanes, α,β-unsaturated nitroalkenes from alkenes, 10,11 as well as β-substituted nitro compounds from α,β-unsaturated nitroalkenes. 12 In addition, several novel transformations were carried out in an efficient way. Those include double functional group

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“…[5] Despite their usefulness, these strategies suffer from some limitations, that is, much elaboration is occasionally necessary to prepare precursors and the reactions that can be subjected to these conditions are somewhat restricted. Recently, we advanced a novel concept, the integrated chemical process, that allows the integration of ordinary reactions under ordinary conditions which are employed in normal laboratory work.…”

Section: Introductionmentioning

confidence: 99%

Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes

et al. 1999

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A novel one-pot process for synthesis of acetylenes has been achieved in which the following series of steps are integrated: addition of an a-anion of sulfone to aldehyde, trapping of the resulting adduct to incorporate a leaving group, and double elimination of this intermediate. Consolidation of Peterson elimination renders the process much simpler. This method provides a convenient and high-yielding access to a variety of enynes and polyynes as well as to functionally substituted aryl acetylenes containing halogen(s) or acetal groups, which are useful building blocks for aryl acetylene scaffolds. Iteration of the one-pot generation of acetylenic bonds provides a new methodology for the buildup of aryl acetylene skeletons.

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Counterattack reagents in organic synthesis: versatility and efficiency

Cited by 13 publications

References 33 publications

Mono-deoxygenation of Nitroalkanes, Nitrones, and HeterocyclicN-Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent”

Mono-deoxygenation of Nitroalkanes, Nitrones, and HeterocyclicN-Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent”

Recent Developments of Compounds Containing the Nitrogen-Oxygen Moiety in Organic Synthesis

Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes

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