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Reinhard Schmutzler - One of the best experts on this subject based on the ideXlab platform.

  • chemistry of bis pentafluorobenzyl phosphines and phosphine oxides single crystal x ray diffraction study of η6 mesitylene dichloro bis pentafluorobenzyl phosphinous acid ruthenium ii and of 1 2 bis pentafluorophenyl ethane
    Journal of Fluorine Chemistry, 1997
    Co-Authors: Roland Krafczyk, Holger Thönnessen, Peter G Jones, Reinhard Schmutzler
    Abstract:

    Abstract The reaction of pentafluorobenzyl magnesium bromide with Phosphorus Trichloride in a 2:1 molar ratio led to the disubstituted product, bis(pentafluorobenzyl) bromophosphine 1 , which, upon reaction with lithium aluminium hydride, was converted to bis(pentafluorobenzyl) phosphine 3 . The reaction of 3 with oxygen led to bis (pentafluorobenzyl) phosphine oxide 4 . The reaction of 1,3 and 4 with di- μ -chloro-bis-[( η 6 -mesitylene) chloro-ruthenium (II)] 5 yielded the η 6 -mesitylene-phosphinedichloro-rutheniun (II) complexes 6–8 . Single-crystal X-ray structure determinations are described for the phosphinous acid-ruthenium(II) complex 8 and for the by-product 1,2 bis (pentafluorophenyl)ethane 2 , formed during the Grignard reaction of magnesium and pentafluorobenzylbromide. In 8 , the Ru-C bond lengths can be categorised as four short (219–222 pm) and two long (224–228 pm). A weak intramolecular P-OH···Cl contact (O···Cl, 304 pm) is observed.

  • synthesis and structure of tetraorganoguanidinyl substituted Phosphorus halogen compounds and of tris n n n n n tetramethyl guanidinyl phosphonium salts
    Phosphorus Sulfur and Silicon and The Related Elements, 1997
    Co-Authors: Jochen Munchenberg, Peter G Jones, Holger Thönnessen, Reinhard Schmutzler
    Abstract:

    Abstract The N-(N′,N′,N′,N′-tetraorgano)guanidine-substituted dichlorophosphines 3a - 3c were prepared by the reaction of Phosphorus Trichloride with the corresponding guanidine or N-lithiated guanidine. The high-field shift of the α(31P) values of 3a - 3c reflects the strong electron-donating effect of the guanidinyl substituents. Attempts to achieve further substitution of chlorine in PCl3 by N′,N′,N′,N′-tehamethylguanidine (HTMG) 1a (employed as such or as its N-trimethylsilyl derivative, TMSTMG, 2) led to the formation of tris-N-(N′,N′,N′,N′-tetramethyl)guanidinylphosphonium salts such as 4. A salt containing the same cation was obtained from the reaction of bis-N-(N′,N′,N′,N′-tetramethyl)guanidinyltrichlorophosphorane 5 with magnesium. Difluoro-N-(N′,N′,N′,N′-tetramethyl)guanidinylphosphine 6 was obtained from difluorochlorophosphine and HTMG 1a. Hydrolysis of 6 led, depending upon the conditions of the reaction, either to N′,N′,N′,N′-tetramethylguanidinium phosphonofluoridate 7 or tris-N-(N′N,N′,N′-...

  • preparation of n phosphorylated nitrogen mustards with the benzodiaza and oxazaphosphorinone ring systems hydrolysis of 2 chloro benzodiazaphosphorinones
    Phosphorus Sulfur and Silicon and The Related Elements, 1996
    Co-Authors: Ion Neda, Peter G Jones, Ralf Sonnenburg, Axel Fischer, Reinhard Schmutzler
    Abstract:

    Abstract The reaction of N-p-ethoxyphenylanthranilic acid 1 with Phosphorus Trichloride furnished the 2-chloro-1,3,2-benzoxazaphosphorin-6-one 2, which was allowed to react with bis-(2-chloroethyl)amine hydrochloride to form 3 by substitution at Phosphorus. Treatment of 3 and the previously known N-p-fluorobenzyl-, N-p-chlorobenzyl- and N-o-chlorobenzyl-substiuted 1,3,2-benzodiazaphosphorin-4-ones 4–6 with the hydrogen peroxide/urea 1:1 adduct led to the phosphoryl species 7–10. The phosphoryl derivatives 14–16 were obtained by hydrolysis of the previously known λ3P-chloro derivatives 11–13 with small amounts of water. For the N-p-fluorobenzyl substituted compound 14 a single crystal X-ray structure determination showed a weak intermolecular P—H … O contact.

Roland Krafczyk - One of the best experts on this subject based on the ideXlab platform.

Musilová Jitka - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of hydroxy derivatives of 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione
    2008
    Co-Authors: Musilová Jitka
    Abstract:

    Synthesis of hydroxy derivatives of 3-phenyl-2H-1,3-benzoxazine-2,4(3H)- dione Jitka Musilová The thesis is concerned with the preparation of 16 cyclic analogues of hydroxy-salicylanilides, i.e. 3- phenyl-2H-1,3-benzoxazine-2,4(3H)-diones monosubstituted with a hydroxyl group on the heterocyclic ring. The starting hydroxysalicylanilides belonging to four series were synthesized by the microwave- assisted reaction of the respective hydroxysalicylic acid with aniline (unsubstituted or para- substituted by chlorine, methyl or methoxy groups) in the presence of Phosphorus Trichloride. Their treatment with ethyl-chloroformate afforded the expected 1,3-benzoxazine derivatives in 77 - 94 % yields. All compounds prepared were characterized by infrared and NMR spectroscopy and by elemental analysis. All the compounds were examined for antifungal activity in vitro against Candida albicans, C. tropicalis, C. krusei, C. glabrata, Trichosporon asahii, Trichophyton mentagrophytes, Aspergillus fumigates, and Absidia corymbifera, but none of these compounds was more active than ketoconazole. In general, parent hydroxysalicylanilides were more active than their cyclic counterparts

Růžková Barbora - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of 5-hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and their sulfur
    2008
    Co-Authors: Růžková Barbora
    Abstract:

    Synthesis of 5-hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and their sulfur analogues Barbora Růžková The thesis is concerned with the preparation of 5-hydroxy-3-phenyl-2H-1,3-benzoxazine- 2,4(3H)-diones, 5-hydroxy-3-phenyl-4-thioxo-2H-1,3-benzoxazin-2-ones and 5-hydroxy-3- phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones, i.e. cyclic analogues of 2,6-di- hydroxybenzanilides. The starting 2,6-dihydroxybenzanilides were synthesized by the microwave-assisted reaction of 2,6-dihydroxybenzooic acid with aniline (unsubstituted or para-substituted by chlorine, methyl, butyl or methoxy groups) in the presence of Phosphorus Trichloride. Their treatment with ethyl-chloroformate afforded 5-hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)- diones in 77 - 94 % yields. 5-Hydroxy-3-phenyl-4-thioxo-2H-1,3-benzoxazin-2-ones and 5- hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones were obtained by thionation using Lawesson's reagent in 31 - 42 and 24 - 33 % yields, respectively. All the compounds were characterized by infrared and NMR spectroscopy and by elemental analysis. No substance exerted either antimycotic activity (against Candida albicans, C. tropicalis, C. krusei, C. glabrata, Trichosporon asahii, Trichophyton mentagrophytes, Aspergillus fumigates, and Absidia corymbifera) or antimycobacterial activity..

Alexey B. Dobrynin - One of the best experts on this subject based on the ideXlab platform.

  • regiochemistry of the reaction of 3 4 6 triisopropyl 1 2 benzoquinone with phenylacetylene in the presence of Phosphorus Trichloride
    ChemInform, 2012
    Co-Authors: V F Mironov, Alexey B. Dobrynin, V K Cherkasov, A V Bogdanov, N N Vavilina, I A Litvinov
    Abstract:

    The reaction of 3,4,6-triisopropyl-1,2-benzoquinone with phenylacetylene and Phosphorus Trichloride gave 2,6-dichloro-5,7,8-triisopropyl-4-phenyl-1,2λ5-benzoxaphosphinine 2-oxide whose structure was determined by X-ray analysis.

  • Reactions of 3,5-di( tert -butyl)-1,2-benzoquinone with terminal acetylenes in the presence of Phosphorus Trichloride. ipso -Substitution of the tert -butyl group
    Russian Chemical Bulletin, 2007
    Co-Authors: Vladimir F. Mironov, Alfia A. Shtyrlina, E. N. Varaksina, Andrei V. Bogdanov, A. V. Nemtarev, Vladimir K. Cherkasov, Alexey B. Dobrynin, Dmitry B. Krivolapov, Rashid Z. Musin, Igor A. Litvinov
    Abstract:

    The reactions of 3,5-di(tert-butyl)-1,2-benzoquinone with aryl-and alkylacetylenes in the presence of Phosphorus Trichloride afford 4-aryl(alkyl)-8-tert-butyl-2,6-dichloro-2-oxo-2H-benzo[e][1,2]oxaphosphinines as the major ipso-substitution products of the tert-butyl group by the chlorine atom. 4-Aryl(alkyl)-6,8-di(tert-butyl)-2,5-dichloro-2-oxo-and 4-aryl(alkyl)-6-tert-butyl-2,8-dichloro-2-oxo-2H-benzo[e][1,2]oxaphosphinines were obtained as the minor products. The structures of the stable representatives of this series were confirmed by X-ray diffraction.

  • new reaction in the ternary system phenanthrenequinone Phosphorus Trichloride arylacetylene
    Doklady Chemistry, 2002
    Co-Authors: V F Mironov, Alexey B. Dobrynin, F F Alekseev, N M Azancheev, I A Litvinov, A T Gubaidullin, T A Baronova, R Z Musin, Sh K Latypov, A I Konovalov
    Abstract:

    It is known that the interaction of ortho -quinones with derivatives of trivalent Phosphorus occurs rather readily and usually results in the formation of phosphoranes [1]. These derivatives of pentacoordinated Phosphorus atom containing dioxaphospholene cycles are used in organic synthesis [2]. Recently, we showed that the reaction of phenanthrenequinone ( I ) with Phosphorus Trichloride and phenylacetylene as a third component under mild conditions ( 20°e ) yields a new heterocyclic system, 1,2-oxaphosphatriphenylene ( IIa ) [3]. Its content in the reaction mixture ranges up to 40–45%. Together with the formation of the phosphoryl group and the P–C bond, carbon is substituted for one of the oxygen atoms in phenanthrenequinone and chlorine is introduced selectively into the seventh position of the 1-oxa2-phosphatriphenylene heterocycle ( II ). The product of the interaction of quinone I with Phosphorus Trichloride, phosphorane III , which can be formed as an intermediate, is unstable and undergoes complex transformations in the absence of phenylacetylene.

  • regiochemistry of the reaction of 3 6 bis tert butyl 1 2 benzoquinone with Phosphorus Trichloride in the presence of arylacetylene
    Doklady Chemistry, 2002
    Co-Authors: V F Mironov, Alexey B. Dobrynin, V K Cherkasov, F F Alekseev, N M Azancheev, I A Litvinov, A T Gubaidullin, A A Konovalov
    Abstract:

    The reaction of Phosphorus pentachloride with arylacetylenes followed by hydrolysis of the initially formed phosphonium products is considered as an important method for the synthesis of derivatives of unsaturated phosphonium acids which can be used as initial compounds to prepare various types of new promising biologically active organoPhosphorus products [1]. The replacement of two chlorine atoms in Phosphorus pentachloride by the phenylenedioxy fragment results unexpectedly in 2,6-dichloro-2oxobenzo[ e ]-1,2-oxaphosphorines, which are products of multistep transformations including easy formation of the P‐C bond and the phosphoryl group, ipso -substitution of the oxygen atom, and regioselective chlorination of the aromatic ring in the para -position relative to endocyclic oxygen of the phosphorine heterocycle [2‐ 4]. A similar synthetic outcome can be attained in the phenanthrenequinone‐Phosphorus Trichloride‐arylacetylene ternary system, in which isolation of the