ChemInform Abstract: Reaction of N,N‐Dialkylcarboxamides with Halogens.

Burakov, N. I.; Kanibolotskii, A. L.; Osichenko, G. Yu.; Mikhailov, V. A.; Savëlova, V. A.; Kosmynin, V. V.

doi:10.1002/chin.200219026

Cited by 2 publications

(3 citation statements)

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“…Among many structures tested, only N,N′-diacylpiperazines produce relatively stable complexes with bromine (as well as with iodine and interhalogens). 51 Adducts of N,N′-diacylpiperazines with halogens (interhalogens) have been obtained as shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

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Multiple Noncovalent Bonding in Halogen Complexes with Oxygen Organics. I. Tertiary Amides

Suponitsky

Burakov²,

Kanibolotsky

et al. 2016

J. Phys. Chem. A

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The present work describes the structure and binding of adducts of N,N′-diacetylpiperazine with halogens and interhalogens based on combination of different experimental methods and quantum chemical calculations. On the basis of conductometric and spectro-photometric experimental results, behavior of complexes in the acetonitrile solution was described. The iodine adduct with N,N′-diacetylpiperazine fully degrades into components. Adducts of interhalogens I–X (X = Cl or Br) with N,N′-diacetylpiperazine in acetonitrile partially dissociate to anionic [X–I–X]− and cationic species. In the solid state, molecules are connected via CO···I, C–H···I, and Cl···Cl attractive interactions. N,N′-diacetylpiperazine···dihalogen complex is stabilized by simultaneous CO···I and C–H···I interactions. Such binding mode allows to explain the problems of the direct halogenation of acetyl-containing compounds with molecular halogens as reagents. We believe that the observed binding pattern can be used as prototypical for future design of halogeno complexes.

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Section: Resultsmentioning

confidence: 99%

“…Synthetic procedures have been described in our earlier study. 51 For the purposes of this paper, some necessary information as well as spectroscopy data of solid adducts is included in Supporting Information (Section S1) 3.2. Molecular and Crystal Structure of Compounds IIIa and IIIb.…”

Section: Resultsmentioning

confidence: 99%

Multiple Noncovalent Bonding in Halogen Complexes with Oxygen Organics. I. Tertiary Amides

Suponitsky

Burakov²,

Kanibolotsky

et al. 2016

J. Phys. Chem. A

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“…8 As an example, the mono-α-bromination of carboxamides is frequently achieved with Br 2 or N-bromo succinimide (NBS). In both cases, overbromination can lead to lower yields, and the oxidative potential of those reagents means that the functional group tolerance is moderate (namely, but not only, toward unsaturations) 9,10 With these commonly used methods, the chemoselective α-bromination of amides over other carbonyl groups remains a challenging transformation.…”

Section: ■ Introductionmentioning

confidence: 99%

Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

et al. 2019

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Functionalization at the α-position of carbonyl compounds has classically relied on enolate chemistry. As a result, the generation of a new C–X bond, where X is more electronegative than carbon requires an oxidation event. Herein we show that, by rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides. More than 60 examples are presented to establish the generality of this process, and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodology.

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ChemInform Abstract: Reaction of N,N‐Dialkylcarboxamides with Halogens.

Cited by 2 publications

References 1 publication

Multiple Noncovalent Bonding in Halogen Complexes with Oxygen Organics. I. Tertiary Amides

Multiple Noncovalent Bonding in Halogen Complexes with Oxygen Organics. I. Tertiary Amides

Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

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