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Миронов, В. Ф.; Petrov, Ravil R.; Shtyrlina, A. A.; Литвинов, И. А.; Gubaidullin, А. Т.; Varaksina, E. N.; Konovalov, A. I.

doi:10.1023/a:1011377231921

Cited by 4 publications

(5 citation statements)

References 3 publications

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“…Note that the direct 1 J PC 3 constants of bromophosphorines IX3 XII are invariably lower by 12. 5 Hz than those of chlorophosphorines IV, whereas the 1 J HC 3 constants of these two groups of compounds are equal to each other, which agrees with the results in [2].…”

Section: /3 S S (A I a J )B(i J) (A 2 ) And Thermal Parameters Ofsupporting

confidence: 91%

“…The O 2 and O 3 atoms of the exocyclic substituents deviate by 30.279(2) and 1.956(2)A from the P 2 C 3 C 4 C 4a plane and by 30.947(2) and 1.394(2) A from the P 2 C 3 C 4 C 4a plane, respectively. Such deviations of the O 3 and O 2 atoms point to an axial position of the hydroxy group and an equatorial position of the phosphoryl oxygen, which completely agrees with published data for analogous structures studied [2,4,5]. The principal geometric parameters of the heteroring in these compounds are almost the same.…”

Section: /3 S S (A I a J )B(i J) (A 2 ) And Thermal Parameters Ofsupporting

confidence: 89%

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Reaction of (phenylenedioxy)trihalophosphoranes with arylacetylenes: VI. Regiochemistry of the reaction of 2,2,2-trihalo-5-methylbenzo[d][1,3,2]dioxaphospholes with arylacetylenes

et al. 2004

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NMR and IR spectroscopy and X-ray diffraction were used to show that the reaction of 2,2,2-trichloro-and 2,2,2-tribromo-5-methylbenzo[d] [1,3,2]dioxaphospholes with para-substituted arylacetylenes proceeds with regioselective formation of 4-aryl-2-halo-7-methyl-2-oxobenzo[e][1,2]oxaphosphorines. With the trichlorophosphole, selective chlorination of the phenylene fragment in the para position to the endocyclic oxygen atom occurs. With the tribromophosphole, 6-bromo-and unsubstituted benzo[e][1,2]oxaphosphorines are formed as major products. The molecular and supramolecular structure of some of the obtained oxaphosphorines was studied by X-ray diffraction.We recently showed [2] that the reaction of 2,2,2-trichlorobenzo[d][1,3,2]dioxaphosphole (I) with arylacetylenes unexpectedly provides 4-aryl-2,6-dichlorobenzo[e][1,2l 5 ]oxaphosphorine 2-oxides. This mechanistically rather complex reaction involves facile formation of the phosphoryl group and carbon3phos-phorus bond, ipso substitution of the oxygen atom, and regioselective chlorination of the phenylene substituent in the para position to the oxygen atom of the foming benzo[e][1,2]oxaphosphorine ring. Introduction of one, two, or four halogen atoms in the ophenylene fragment of starting phosphole I does not alter the reaction pathway [335], but the regioselective chlorination of the benzo fragment to form 4-aryl-2,6,7-trihalobenzo[e][1,2]oxaphosphorines takes place only if it bears only one halogen substituent.In this work we present the results of investigation of the effect of the electron-donor methyl substituent in the phenylene fragment of 2,2,2-trichloro-and 2,2,2-tribromo-5-methylbenzo[d][1,3,2]dioxophospholes (II, III) on the synthetic result of their reaction with arylacetylenes. It was found that the reaction of compound II with arylacetylenes proceeds with a high degree of regioselectivity and leads mainly (or exclu-ÄÄÄÄÄÄÄÄÄÄÄÄ 1 For communication V, see [1].

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Section: /3 S S (A I a J )B(i J) (A 2 ) And Thermal Parameters Ofsupporting

confidence: 91%

Section: /3 S S (A I a J )B(i J) (A 2 ) And Thermal Parameters Ofsupporting

confidence: 89%

Reaction of (phenylenedioxy)trihalophosphoranes with arylacetylenes: VI. Regiochemistry of the reaction of 2,2,2-trihalo-5-methylbenzo[d][1,3,2]dioxaphospholes with arylacetylenes

et al. 2004

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“…Thus, the alternating spatial separation of the regions having predominantly hydrophilic and hydrophobic properties is observed in the crystal packing of 3, as in other structures studied earlier. 6,7 The minor condensation product of 2 methylresor cinol with p tolualdehyde was identified as rccc isomer 2 by 1 H and 13 C NMR spectroscopy and mass spectrometry as well as by analogy with the published data. [2][3][4][5] The 1 H NMR spectra of isomeric calixarenes 1 and 2 are similar to the spectra of analogous isomers described earlier, 2-4 but differ substantially from each other.…”

Section: Resultsmentioning

confidence: 65%

Synthesis of rctt, rccc, and rcct diastereomers of calix[4]methylresorcinarenes based on p-tolualdehyde. X-ray diffraction study of the rcct isomer. Formation of rctt and rccc cavitands in a cone conformation

et al. 2005

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Synthesis of rctt, rccc, and rcct diastereomers of calix[4]methylresorcinarenes based on p tolualdehyde. X ray diffraction study of the rcct isomer. Formation of rctt and rccc cavitands in a cone conformationThe reaction of 2 methylresorcinol with p tolualdehyde afforded rctt and rccc diastereo mers of calix[4]methylresorcinarene and an insignificant amount of the rcct isomer. The structure of the latter was established by X ray diffraction analysis. The macrocycle in the rcct isomer adopts a 1,2 diplanar conformation, in which one pair of adjacent resorcinol fragments is nearly orthogonal to another pair of resorcinol fragments. The supramolecular organization of the diastereomer in the crystal was studied. The tolyl fragments form the outer surface of the layers composed of the macrocycles, which are separated by "interlayers" of solvent molecules. Cavitands adopting a cone conformation were prepared from the rctt and rccc diastereomers by linking the adjacent phenoxy groups through methylene bridges. The structure of the rctt cavitand was confirmed by 2D NMR spectroscopy.

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“…The intermediate 11 should be in equilibrium with quasi phosphonium salt (12). Depending on which substituent is at the multiple bond, an aryl or an alkyl, two directions of subsequent transformatons of intermediate 12 are pos sible.…”

Section: Methodsmentioning

confidence: 99%

“…halogenation, moreover, in some cases, their substitution for the halogen takes place. [11][12][13] Another approach to the preparation of benzooxa phosphinine 2 oxide derivatives consists in the reaction of three component system 3,5 di(tert butyl) 1,2 benzo quinone or 3,6 di(tert butyl) 1,2 benzoquinone (1)-phosphorus trichloride-arylacetylene suggested recently. 14-18…”

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confidence: 99%

Reaction of 3,6-di(tert-butyl)-1,2-benzoquinone with terminal alkylacetylenes in the presence of phosphorus trichloride

et al. 2009

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A reaction of 3,6 di(tert butyl) 1,2 benzoquinone with alkynes in the presence of phosphorus trichloride leads to a predominant formation of 4 alkyl and 4 haloalkyl 5,8 di(tert butyl) 2,6 dichloro 2H benzo[e][1,2]oxaphosphinine 2 oxide. An ipso substitution of the tert butyl group at ortho position to the oxygen atom of the benzophosphinine system with the formation of 4 alkyl 5 tert butyl 2,8 dichloro 2H benzo[e][1,2]oxaphosphinine 2 oxide was the minor route of the reaction with alkylacetylenes. Molecular structures of 4 butyl 5,8 di(tert butyl) 2,6 dichloro 2H benzo[e][1,2]oxaphosphinine 2 oxide and 5,8 di(tert butyl) 2,6 dichloro 4 hexyl 2H benzo[e][1,2]oxaphosphinine 2 oxide were studied by X ray analysis.

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Cited by 4 publications

References 3 publications

Reaction of (phenylenedioxy)trihalophosphoranes with arylacetylenes: VI. Regiochemistry of the reaction of 2,2,2-trihalo-5-methylbenzo[d][1,3,2]dioxaphospholes with arylacetylenes

Reaction of (phenylenedioxy)trihalophosphoranes with arylacetylenes: VI. Regiochemistry of the reaction of 2,2,2-trihalo-5-methylbenzo[d][1,3,2]dioxaphospholes with arylacetylenes

Synthesis of rctt, rccc, and rcct diastereomers of calix[4]methylresorcinarenes based on p-tolualdehyde. X-ray diffraction study of the rcct isomer. Formation of rctt and rccc cavitands in a cone conformation

Reaction of 3,6-di(tert-butyl)-1,2-benzoquinone with terminal alkylacetylenes in the presence of phosphorus trichloride

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