New Phosphorus−Carbon Cage Compounds by Diels−Alder and Homo Diels−Alder Reactions of 1,3,5-Triphosphabenzenes with Alkenes

Peters, Christoph; Disteldorf, Hendrik; Fuchs, Evelyn; Werner, Stefan; Stutzmann, Stefanie; Bruckmann, Joachim; Binger, Paul; Heydt, H.; Regitz, Manfred

doi:10.1002/1099-0690(200109)2001:18<3425::aid-ejoc3425>3.0.co;2-u

Cited by 21 publications

(5 citation statements)

References 11 publications

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“…The shifts of these signals are, however, similar to those seen for other g 4 -coordinated (P=C) 2 fragments of phosphabarrelenes. 17 One other apparent anomaly in the 31 P{ 1 H} NMR spectrum of 8 is the very small 1 J PP coupling constants between the three contiguous P-centres. The magnitudes of these couplings presumably arise from the acute angles about the central P-atom which lead to a high degree of p-character to the two bonds between these three P-atoms.…”

Section: Resultsmentioning

confidence: 99%

Differing reactivities of PCMe and PCBu^ttowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P₅C₅Me_nBu^t_5−n, n = 0, 1 or 2)

2007

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The reaction of excess P[triple band]CMe with the triphosphabenzene, 1,3,5-P3C3Bu(t)3, yields a phosphaalkyne pentamer, P5C5Me2Bu(t)3, which displays a pentaphosphaisolumibullvalene core structure. Its treatment with [W(CO)5(THF)] gives a complex of this cage, [{W(CO)5}2(mu-eta1:eta1-P5C5Me2Bu(t)3)], which has been structurally characterised. In contrast, the previously reported reaction of P[triple band]CBu(t) with 1,3,5-P3C3Bu(t)3, affords, in addition to the known tetraphosphabarrelene, 1,3,5,7-P4C4Bu(t)4, a new phosphaalkyne pentamer (P55C5Bu(t)5), which has a partially unsaturated "open cage" core. Although P[triple band]CBu(t) does not react with 1,3,5,7-P4C4Bu(t)4, the reaction of P[triple band]CMe with the tetraphosphabarrelene is shown to give a mixture of products. Treatment of these with [W(CO)5(THF)] leads to the isolation of the tungsten carbonyl complex, [{W(CO)} {W(CO)4}(mu-eta1:eta4-P5C5MeBu(t)4)], which has been structurally characterised. This study suggests that P[triple band]CMe has a significantly greater reactivity towards cycloadditions than its bulkier counterpart, P[triple band]CBu(t).

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Section: Resultsmentioning

confidence: 99%

Differing reactivities of PCMe and PCBu^ttowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P₅C₅Me_nBu^t_5−n, n = 0, 1 or 2)

2007

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“…150b When tri- tert -butyl-substituted 1,3,5-triphosphabenzene reacted with ethylene, only Diels–Alder cycloaddition took place, and monoadduct 174 was obtained (Scheme 79 ). 150a…”

Section: [4+2] Cycloadditionmentioning

confidence: 99%

Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions

et al. 2021

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“…A single example of transition-metal-catalyzed addition of a carbon pronucleophile to cyclopropene proceeding with preservation of a three-membered ring was recently shown by Chisholm . Herein, we report an efficient and atom-economic approach to cyclopropylphosphonates and cyclopropylphosphine oxides via the diastereoselective palladium-catalyzed hydrophosphorylation and hydrophosphinylation of cyclopropenes …”

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confidence: 96%

Palladium-Catalyzed Hydrophosphorylation and Hydrophosphinylation of Cyclopropenes

2008

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New Phosphorus−Carbon Cage Compounds by Diels−Alder and Homo Diels−Alder Reactions of 1,3,5-Triphosphabenzenes with Alkenes

Cited by 21 publications

References 11 publications

Differing reactivities of PCMe and PCBu^ttowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P₅C₅Me_nBu^t_5−n, n = 0, 1 or 2)

Differing reactivities of PCMe and PCBu^ttowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P₅C₅Me_nBu^t_5−n, n = 0, 1 or 2)

Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions

Palladium-Catalyzed Hydrophosphorylation and Hydrophosphinylation of Cyclopropenes

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New Phosphorus−Carbon Cage Compounds by Diels−Alder and Homo Diels−Alder Reactions of 1,3,5-Triphosphabenzenes with Alkenes

Cited by 21 publications

References 11 publications

Differing reactivities of PCMe and PCButtowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P5C5MenBut5−n, n = 0, 1 or 2)

Differing reactivities of PCMe and PCButtowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P5C5MenBut5−n, n = 0, 1 or 2)

Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions

Palladium-Catalyzed Hydrophosphorylation and Hydrophosphinylation of Cyclopropenes

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Differing reactivities of PCMe and PCBu^ttowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P₅C₅Me_nBu^t_5−n, n = 0, 1 or 2)

Differing reactivities of PCMe and PCBu^ttowards a triphosphabenzene and a tetraphosphabarrelene: synthesis of new phosphaalkyne pentamers (P₅C₅Me_nBu^t_5−n, n = 0, 1 or 2)