Untersuchungen an Diazomethanen, XXIX. Reaktionen mit dem tautomeren Diazomethyl‐Anion

Beutler, Rolf; Zeeh, Bernd; Müller, Eugen

doi:10.1002/cber.19691020819

Cited by 18 publications

(1 citation statement)

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“…It should be noted that already in 1969 Müller et al had formulated an intermediate (1,3,4‐oxdiazoline) similar to the [3+2]‐cycloadducts 8 – 10 in order to explain the nature of the products (benzophenone imine, Ph 2 C=N–NH–CHO, etc.) of the reaction of lithium isocyano amide (“lithio nitrile imine”, Li + CNNH – ) with benzophenone 5c. In our case, clearly no 1,3‐dipolar cycloaddition occurred between the metallo (pentacarbonylchromio) nitrile imine and the ketone (acetone) (see above and 6 , 7 )…”

Section: Resultsmentioning

confidence: 56%

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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Section: Resultsmentioning

confidence: 56%

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 First Solid-State Structure of a Lithiated Diazomethane with C–Li and N–Li Bonds: {[Me3SiC(Li)N2]2·3 THF}∞

et al. 1998

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Lithium‐diazoessigsäure‐äthylester

Schöllkopf

Frasnelli

1970

Angewandte Chemie

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Untersuchungen an Diazomethanen, XXIX. Reaktionen mit dem tautomeren Diazomethyl‐Anion

Abstract: Arbeitet man analog, 1aBt aber bei $ 2 0 stehen, so findet man neben 51

Cited by 18 publications

References 5 publications

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]

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]

The First Solid-State Structure of a Lithiated Diazomethane with C–Li and N–Li Bonds: {[Me3SiC(Li)N2]2·3 THF}∞

Lithium‐diazoessigsäure‐äthylester

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Untersuchungen an Diazomethanen, XXIX. Reaktionen mit dem tautomeren Diazomethyl‐Anion

Abstract: Arbeitet man analog, 1aBt aber bei $ 2 0 stehen, so findet man neben 51

Cited by 18 publications

References 5 publications

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]

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]

The First Solid-State Structure of a Lithiated Diazomethane with C–Li and N–Li Bonds: {[Me3SiC(Li)N2]2·3 THF}∞

Lithium‐diazoessigsäure‐äthylester

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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]

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]