Notiz über die Reaktion der (Pentahalogenäthylimido)phosphorsäure‐trichloride mit Ammoniumchlorid zu sechsgliedrigen C,N,P‐Ringsystemen

Schöning, Georg; Glemser, Oskar

doi:10.1002/cber.19761090832

Cited by 22 publications

(2 citation statements)

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“…Ausgangsverbindungen für die hier beschriebenen Synthesen sind das 2,2-Difluor-4,6-bis(trifluormethyO-l^^^A^-triazaphosphinin (1) [1] bzw. das 2,2-Dichlor-4,6-bis(trifluormethyl)-l,3,5,2A 5 -triazaphosphinin (2) [1].…”

Section: Ergebnisse Und Diskussionunclassified

Triazaphosphinine – Reaktionen, Zwitterionen, P–B-Austausch/ Triazaphosphinines – Reactions, Zwitter Ions, P – B-Exchange

Meyer

Kadel

Oberhammer

1988

Zeitschrift Für Naturforschung B

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Abstract2,2-Dichloro-triazaphosphinine (2) reacts with SbF3 in the molar ratio 3:1 to give the mixed halogenated triazaphosphinine (3). New addition compounds 5 and 6 can be formed in the reaction of the zwitter ion 4 and amines or in the reaction of 2.2-difluoro-triazaphosphinine (1) with KCN. Phosphorus-boron-exchange is observed in the reactions of 4 or 2 with BF3 · OEt2. The new C-B -N-heterocycles 8 and 9 are obtained. The gas-phase structure of 1 has been determined by electron diffraction. The scattering intensities are compatible with a planar ring conformation with C2v symmetry and with equivalent NC bond lengths (PN = 1.579(10) Å, NC = 1.299(7) Å, NPN = 109.2(7)°, PNC - 118.1(9)°, CNC - 119.6(7)° and NCN = 127.5(12)°).

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Section: Ergebnisse Und Diskussionunclassified

Triazaphosphinine – Reaktionen, Zwitterionen, P–B-Austausch/ Triazaphosphinines – Reactions, Zwitter Ions, P – B-Exchange

Meyer

Kadel

Oberhammer

1988

Zeitschrift Für Naturforschung B

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“…The synthesis of the title compound, namely the 1,3,2λ 5 -diazaphosphete F has been claimed in 1973; however, soon after Glemser demonstrated that it was in fact a mixture of 6-membered rings G and H . Although the mechanism of the reaction has not been elucidated, it seemed quite possible that the observed products G and H resulted from a disproportionation of the 4-π-electron 4-membered ring F , arguing again for the high instability of the 4-π-electron 4-membered heterocycles.…”

Section: Introductionmentioning

confidence: 99%

X-ray Crystal Structure, ab Initio Calculations, and Reactivity of 1,3,2λ⁵-Diazaphosphetes: A New Type of 4-π-Electron 4-Membered Heterocycle

et al. 1996

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The structure of P,P-bis(diisopropylamino)-4-phenyl-1,3,2lambda(5)-diazaphosphete, 1a, has been determined by a single-crystal X-ray diffraction study (C(19)H(33)N(4)P, monoclinic system, space group P2(1), a = 9.482(1) Å, b = 11.374(3) Å, c = 9.668(2) Å, beta = 97.16(1) degrees, Z = 2). According to quantum chemical calculations at an RHF level of optimization utilizing the 6-31g(d,p) basis set, 1a has a zwitterionic structure with the negative charge delocalized on the NCN allylic fragment and the positive charge localized at the phosphorus. Heterocycle 1a reacts with water and benzaldehyde affording N-phosphoranylbenzamidine 3 (95% yield) and the expected aza-Wittig adduct 4 (85% yield), respectively. Addition of 1 equiv of methyl trifluoromethanesulfonate and of 2 equiv of BH(3).THF to 1a affords cyclic phosphonium salt 5 (94% yield) and the bis(borane) adduct 6a (90% yield), respectively. Dimethyl acetylenedicarboxylate slowly reacts with 1a giving rise to 1,3,4lambda(5)-diazaphosphinine, 9, in 70% yield. The X-ray crystal structures of products 2,3, and 6a are reported (2: C(26)H(38)N(5)P, monoclinic system, space group C2/c, a = 16.337(8) Å, b = 19.810(2) Å, c = 8.800(2) Å, beta = 117.68(2) degrees, Z = 4. 3: C(19)H(35)N(4)OP, orthorhombic system, space group P2(1)2(1)2(1), a = 9.090(1) Å, b = 12.955(2) Å, c = 17.860(3) Å, Z = 4. 6a: C(19)H(39)B(2)N(4)P, orthorhombic system, space group P2(1)2(1)2(1), a = 10.340(1) Å, b = 13.247(1) Å, c = 16.996(1) Å, Z = 4).

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Ein imino‐überbrücktes Triaza‐λ⁵‐phosphetin

Niecke

Schäfer

1977

Angewandte Chemie

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Notiz über die Reaktion der (Pentahalogenäthylimido)phosphorsäure‐trichloride mit Ammoniumchlorid zu sechsgliedrigen C,N,P‐Ringsystemen

Abstract: Kukhar und Mitarbb. I) berichten, durch Umsetzung von (Pentachlorathy1imido)phosphorsauretrichlorid mit NH,CI das 4-gliedrige Ringsystem 2,2-Di~hlor-4-trichlormethyl-l,3,2~~-diazaphosphet gemal3 (1) erhalten zu haben.

Cited by 22 publications

References 3 publications

Triazaphosphinine – Reaktionen, Zwitterionen, P–B-Austausch/ Triazaphosphinines – Reactions, Zwitter Ions, P – B-Exchange

Triazaphosphinine – Reaktionen, Zwitterionen, P–B-Austausch/ Triazaphosphinines – Reactions, Zwitter Ions, P – B-Exchange

X-ray Crystal Structure, ab Initio Calculations, and Reactivity of 1,3,2λ⁵-Diazaphosphetes: A New Type of 4-π-Electron 4-Membered Heterocycle

Ein imino‐überbrücktes Triaza‐λ⁵‐phosphetin

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Notiz über die Reaktion der (Pentahalogenäthylimido)phosphorsäure‐trichloride mit Ammoniumchlorid zu sechsgliedrigen C,N,P‐Ringsystemen

Abstract: Kukhar und Mitarbb. I) berichten, durch Umsetzung von (Pentachlorathy1imido)phosphorsauretrichlorid mit NH,CI das 4-gliedrige Ringsystem 2,2-Di~hlor-4-trichlormethyl-l,3,2~~-diazaphosphet gemal3 (1) erhalten zu haben.

Cited by 22 publications

References 3 publications

Triazaphosphinine – Reaktionen, Zwitterionen, P–B-Austausch/ Triazaphosphinines – Reactions, Zwitter Ions, P – B-Exchange

Triazaphosphinine – Reaktionen, Zwitterionen, P–B-Austausch/ Triazaphosphinines – Reactions, Zwitter Ions, P – B-Exchange

X-ray Crystal Structure, ab Initio Calculations, and Reactivity of 1,3,2λ5-Diazaphosphetes: A New Type of 4-π-Electron 4-Membered Heterocycle

Ein imino‐überbrücktes Triaza‐λ5‐phosphetin

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X-ray Crystal Structure, ab Initio Calculations, and Reactivity of 1,3,2λ⁵-Diazaphosphetes: A New Type of 4-π-Electron 4-Membered Heterocycle

Ein imino‐überbrücktes Triaza‐λ⁵‐phosphetin