New inorganic metallacycles and the first six-membered covalent "true" heterocycle - Oxidation of RC(E)NHPPh2 (E = O or S; R = H2N, Ph, or Py) with O, S, or Se to give RC(E)NHP(E ')Ph-2 (E ' = O, S, Se) and their coordination chemistry

BIRDSALL, David J., Jason GREEN, Tuan Q. LY, Josef NOVOSAD, Marek NEČAS, A. M. Z. SLAWIN, J. D. WOOLLINS and Zdirad ŽÁK. New inorganic metallacycles and the first six-membered covalent "true" heterocycle - Oxidation of RC(E)NHPPh2 (E = O or S; R = H2N, Ph, or Py) with O, S, or Se to give RC(E)NHP(E ')Ph-2 (E ' = O, S, Se) and their coordination chemistry. Eur. J. Inorg. Chem. Germany: Wiley-VCH Verlag GMBH, 1999, vol. 1999, No 9, p. 1445-1452. ISSN 1434-1948.

Basic information

• Original name: New inorganic metallacycles and the first six-membered covalent "true" heterocycle - Oxidation of RC(E)NHPPh2 (E = O or S; R = H2N, Ph, or Py) with O, S, or Se to give RC(E)NHP(E ')Ph-2 (E ' = O, S, Se) and their coordination chemistry
• Authors: BIRDSALL, David J., Jason GREEN, Tuan Q. LY, Josef NOVOSAD (203 Czech Republic, guarantor), Marek NEČAS (203 Czech Republic), A. M. Z. SLAWIN, J. D. WOOLLINS and Zdirad ŽÁK (203 Czech Republic).
• Edition: Eur. J. Inorg. Chem. Germany, Wiley-VCH Verlag GMBH, 1999, 1434-1948.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10402 Inorganic and nuclear chemistry
• Country of publisher: Germany
• Confidentiality degree: is not subject to a state or trade secret
• RIV identification code: RIV/00216224:14310/99:00001176
• Organization unit: Faculty of Science
• UT WoS: 000083540900007
• Keywords in English: metallacycles; solid-state structures; heterocycles; oxidations
• Tags: heterocycles, metallacycles, oxidations, solid-state structures

Abstract

Direct oxidation of PhC(O)NHPPh2, H2NC(S)NHPPh2, (CSH4N)C(S)NHPPh2 with O-2, S-8, or Se gives [PhC(O)NHP(O)Ph-2] (1), [H2NC(S)NHP(S)Ph-2] (2), [H2NC(O)NHP(S)Ph-2] (3), [PhC(O)NHP(S)Ph-2] (4), [(C5H4N)C(S)NHP(S)Ph-2] (5), and [H2NC(S)NHP(Se)Ph-2] (6). Deprotonation of 1, 2, 4-6 with potassium tert-butoxide gives K[PhC(O)NP(O)Ph-2] (7), K[H2NC(S)NP(S)Ph-2] (8), K[PhC(O)NP(S)Ph-2] (9), K[(C5H4N)C(S)NP(S)Ph-2] (10), and K[H2NC(S)NP(Se)Ph-2] (11). Reaction of 4 with KOBu and [Cu(Ph3P)(2)][NO3] gives [Cu(Ph3P)(PhC(O)NP(S)Ph-2)] (12) which is the first crystallographically characterised example of a non-ionic six-membered "true" heterocycle (i.e. a ring in which every heterocatom is different). 9 and 10 were treated with [PdCl2(COD)] to give [Pd{PhC(O)NP(S)Ph-2}(2)] (13) and [Pd{(C5H4N)C(O)NP(S)Ph-2}(2)] (14), respectively The anion of 8 coordinates to zinc forming [Zn{H2NC(S)NP(S)Ph-2}(2)] (15). Treatment of 2 or 8 with [PtCl2(COD)] gives [Pt{H2NC(S)NP(S)Ph-2}{H2NC(S)NHP(S)Ph-2}]Cl-+(-) (16) and [Pt{H2NC(S)NP(S)Ph-2}(2)] (17), respectively. The X-ray structures of 12, 15-17 are reported.

Links

• GA203/97/0955, research and development project: Name: Studium syntézy, struktury a vazebných poměrů ve sloučeninách obsahujících současně dusík, fosfor, chalkogen a/nebo halogen

Investor: Czech Science Foundation, Synthesis ,structure and bonding of compounds containing phosphorus,nitrogen,chalcogene and/or halogene atoms

• GA203/98/0676, research and development project: Name: Krystalová struktura a vazebné poměry sloučenin nekovů V., VI. a VII. grupy periodického systému

Investor: Czech Science Foundation, Crystal structures and bonding in non-metal compounds of the V., VI. , and VII. group of the periodic systém

• GA203/99/0067, research and development project: Name: Pronájem krystalografických databází
• MSM 143100011, plan (intention): Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles