Zur reaktivität des knallsäureamids umsetzung von saccharin bzw. thiosaccharin mit N-isocyanaminen

Müller, Eugen; Nespital, V.; Beutler, Rolf

doi:10.1016/s0040-4039(01)96486-x

Cited by 6 publications

(1 citation statement)

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“…Our recent finding in the saccharin chemistry was the observation of unusual metalfree "two saccharin-one cyanamide" coupling between sacH and NCNR 2 to grant guanidinated saccharin derivatives [8]. The distinctive feature of this transformation is its formal three-component character, while other known examples of reactivity of sacH toward multiple bond substrates includes the additions to amino alkynes [9,10], isocyanide [11], isocyanates [12], and carbodiimides [12,13]; all these examples include two-component 1:1 additions.…”

Section: Introductionmentioning

confidence: 99%

Copper(II) Prevents the Saccarine-Dialkylcyanamide Coupling by Forming Mononuclear (Saccharinate)(Dialkylcyanamide)copper(II) Complexes

Toikka¹,

Spiridonova²,

Novikov³

et al. 2021

Inorganics

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The reaction in the system CuII/sacNa(H)/NCNR2 (sacNa(H) = sodium saccharinate (saccharin); R = Me, Et) results in the formation of the complexes [Cu(sac)2(NCNR2)(H2O)2] (R = Me 1, Et 2) instead of the expected products derived from the saccharin–cyanamide coupling. Complexes 1, 2, and hydrate 1·2H2O were characterized by IR, AAS (Cu%), TGA, and also by single-crystal X-ray diffraction for 1 and 1·2H2O. An integrated computational study of model structure 1 in the gas phase demonstrates that the Cu–Ncyanamide and Cu–Nsac coordination bonds exhibited a single bond character, polarized toward the N atom and almost purely electrostatic, with the calculated vertical total energies for the Cu–Ncyanamide and Cu–Nsac of 43.6 and 156.4 kcal/mol, respectively. These data confirmed that the copper(II) completely blocks the nucleophilic centers of ligands via coordination, thus preventing the saccharin–cyanamide coupling.

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Section: Introductionmentioning

confidence: 99%

Copper(II) Prevents the Saccarine-Dialkylcyanamide Coupling by Forming Mononuclear (Saccharinate)(Dialkylcyanamide)copper(II) Complexes

Toikka¹,

Spiridonova²,

Novikov³

et al. 2021

Inorganics

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ChemInform Abstract: ZUR REAKTIVITAET DES KNALLSAEUREAMIDS, UMSETZUNG VON SACCHARIN BZW. THIOSACCHARIN MIT N‐ISOCYANAMINEN

Mueller¹,

Nespital²,

Beutler³

1971

Chemischer Informationsdienst. Organische Chemie

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X‐ray Structure of the Isodiazomethane Complex Cr(CO)₅C≡N‐NH₂and [3+2]‐Cycloadditions to the Metallo‐Nitrile‐Imine [Cr(CO)₅C≡N‐NH]^–[1]

Fehlhammer

Schoder

Weinberger

et al. 2009

Zeitschrift anorg allge chemie

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The structure of [Cr(CO) 5 CNNH 2 ] (1a) containing Eugen Müller's "isodiazomethane" as a ligand has been determined by X-ray diffraction. In its deprotonated form 1a acts as a 1,3-dipole of the (metallo) nitrile imine type, i.e., undergoes [3+2]-cycloaddition reactions with acetylenes (MeO 2 CC≡CCO 2 Me), trifluoroacetonitrile, * Prof. Dr. Dr. h.c. W. P. Fehlhammer E-Mail: wpfehlhammer@gmx.de [a] 1367 carbon disulfide and isocyanate (PhNCO). The new 16-electron ligand [C≡N-NH]is isoelectronic with isocyanomethanide [C≡N-CH 2 ]and the fulminate anion [C≡N-O] -. Further relations and derivations within these classes of compounds are discussed. Preparation of Pentacarbonyl(isocyanamine)tungsten (1c): Same procedure as for 1b. The complex is obtained as colourless powder, m.p. 100°C (dec.). Yield: ca. 10 %. C 6 H 2 N 2 O 5 W (365.95): calcd.

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Zur reaktivität des knallsäureamids umsetzung von saccharin bzw. thiosaccharin mit N-isocyanaminen

Cited by 6 publications

References 6 publications

Copper(II) Prevents the Saccarine-Dialkylcyanamide Coupling by Forming Mononuclear (Saccharinate)(Dialkylcyanamide)copper(II) Complexes

Copper(II) Prevents the Saccarine-Dialkylcyanamide Coupling by Forming Mononuclear (Saccharinate)(Dialkylcyanamide)copper(II) Complexes

ChemInform Abstract: ZUR REAKTIVITAET DES KNALLSAEUREAMIDS, UMSETZUNG VON SACCHARIN BZW. THIOSACCHARIN MIT N‐ISOCYANAMINEN

X‐ray Structure of the Isodiazomethane Complex Cr(CO)₅C≡N‐NH₂and [3+2]‐Cycloadditions to the Metallo‐Nitrile‐Imine [Cr(CO)₅C≡N‐NH]^–[1]

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Zur reaktivität des knallsäureamids umsetzung von saccharin bzw. thiosaccharin mit N-isocyanaminen

Cited by 6 publications

References 6 publications

Copper(II) Prevents the Saccarine-Dialkylcyanamide Coupling by Forming Mononuclear (Saccharinate)(Dialkylcyanamide)copper(II) Complexes

Copper(II) Prevents the Saccarine-Dialkylcyanamide Coupling by Forming Mononuclear (Saccharinate)(Dialkylcyanamide)copper(II) Complexes

ChemInform Abstract: ZUR REAKTIVITAET DES KNALLSAEUREAMIDS, UMSETZUNG VON SACCHARIN BZW. THIOSACCHARIN MIT N‐ISOCYANAMINEN

X‐ray Structure of the Isodiazomethane Complex Cr(CO)5C≡N‐NH2and [3+2]‐Cycloadditions to the Metallo‐Nitrile‐Imine [Cr(CO)5C≡N‐NH]–[1]

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X‐ray Structure of the Isodiazomethane Complex Cr(CO)₅C≡N‐NH₂and [3+2]‐Cycloadditions to the Metallo‐Nitrile‐Imine [Cr(CO)₅C≡N‐NH]^–[1]