Several new class of phosphorus heterocyclic compounds containing exocyclic P-C link such as 6-(2'-chloroethyl)/(allyl)/(benzyl)-1,2,4,8,10,11-hexachloro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxides (5-7), 2-(2"-chloroethyl)/(allyl)-6-(1,1-dimethylethyl)-3-cyclohexyl-3,4-dihdro-2H-1,3,2-benzoxazaphosphorin 2-oxides (9, 10), 2-(2"-chloroethyl-2,3-dihydro-3-(4'-bromophenyl)-1H-naphth[1,2-e][1,3,2]-oxazaphosphorin 2-oxide (12), 2-(2"-chloroethyl)/(allyl)-2,3-dihydro-5-benzoyl-1H-1,3,2-benzodiazaphosphole 2-oxides (14, 15), 4-phenyl-2-(2"-chloroethyl)-1H-1,3,3a,5,6-pentaza-2-phosphapentalene 2-oxide (17) and 4-benzyl-2-(2"-chloroethyl)-1H-1,3,3a,5,6-pentaza-2-phospha-pentalene 2-oxide (19) were synthesized by reacting equimolar quantities of corresponding diol (4)/diamines (13, 16, 18), 2-cyclohexylaminomethyl-4-t-butylphenol (8) and 1-(4'-bromoanilinomethyl)-2-naphthol (11), with respective phosponyl dichlorides (1-3) in dry toluene/toluene-tetrahydro-furan/pyridine in the presence of triethylamine at various temperatures. Their structures were established by IR, (1)H-, (13)C- and (31)P-NMR spectral data. The mass spectral data were given for compounds 9, 12 and 15. The title compounds were screened for antibacterial activity against Staphylococcus aureus and Escherichia coli and antifungal activity on Aspergillus niger and Helminthosporium oryzae. Most of the compounds possess significant activity.
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http://dx.doi.org/10.1248/cpb.52.307 | DOI Listing |
Dalton Trans
January 2025
Institut für Anorganische Chemie. Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany.
Compared to aziridines, azaphosphiridines, which formally result from the replacement of a carbon atom by phosphorus, have been much less studied. In this work, accurate values for one of the most prominent properties, the ring strain energy (RSE), have been theoretically examined for a wide range of azaphosphiridine derivatives. Strongly related aspects of interest for developing the use of azaphosphiridines in heteroatom and polymer chemistry are ring opening reactions and polymerisations, the latter facilitated by their significantly high RSE.
View Article and Find Full Text PDFDalton Trans
January 2021
Department of Chemistry, University of Hawai'i at Mānoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, USA.
Exposure of 10π-electron benzazaphosphole 1 to HCl, followed by nucleophilic substitution with the Grignard reagent BrMgCCPh afforded alkynyl functionalized 3 featuring an exocyclic -C[triple bond, length as m-dash]C-Ph group with an elongated P-C bond (1.7932(19) Å). Stoichiometric experiments revealed that treatment of trans-Pd(PEt3)2(Ar)(i) (Ar = p-Me (C) or p-F (D)) with 3 generated trans-Pd(PEt3)2(Ar)(CCPh) (Ar = p-Me (E) or p-F (F)), 5, which is the result of ligand exchange between P-I byproduct 4 and C/D, and the reductively eliminated product (Ar-C[triple bond, length as m-dash]C-Ph).
View Article and Find Full Text PDFOrg Lett
December 2019
Key Laboratory of Organic Chemistry in Jiangxi Province, Institute of Organic Chemistry , Jiangxi Science & Technology Normal University, Nanchang 330013 , China.
An unprecedented palladium-catalyzed intramolecular Ullmann-type cyclization of carbonyl-stabilized phosphonium ylides with aryl bromides was successfully developed. Furthermore, a base-promoted chemoselective hydrolysis of exocyclic P-C bond of the corresponding phosphonium salts delivered various phosphachromones. Excellent selectivity and high efficiency and good functional group tolerance were observed.
View Article and Find Full Text PDFInorg Chem
February 2018
Departamento de Química Orgánica e Inorgánica/IUQOEM, Universidad de Oviedo , E-33071 Oviedo, Spain.
The title complex (1) reacted with [Mn(CO)] under visible-UV irradiation (toluene solution and quartz glassware) to give a mixture of the phosphinidene complex [MnMoCp(μ-κ:κ,η-PMes*)(CO)], the cluster [MnMoCp(μ-κ:κ,η-PMes*)(μ-S)(CO)], and the thiophosphinidene complex [MnMoCp(μ-κ:κ,η-SPMes*)(CO)], in yields of ca. 60, 20, and 10% respectively (Mes* = 2,4,6-CHBu). The major product follows from formal replacement of the SMoCp(CO) fragment in 1 with a Mn(CO) fragment, and displayed multiple bonding to phosphorus (Mn-P = 2.
View Article and Find Full Text PDFPhilos Trans A Math Phys Eng Sci
August 2017
Institut für Anorganische und Analytische Chemie, Universität Münster, Corrensstraße 30, 48149 Münster, Germany
Reaction of MesP─C≡C─Ph (Mes = mesityl) with dineopentylaluminium hydride afforded by hydroalumination a geminal Al/P-based frustrated Lewis pair (FLP; ). Its steric shielding is relatively low, and its reactivity in various secondary reactions is less hindered by steric repulsion than observed for related compounds having bulkier groups attached to aluminium. FLP yielded adducts with MeC─NCO or benzaldehyde via the formation of Al-O and P-C bonds.
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