Synthesis of phosphirenium salts

FONGERS, K. S.; Hogeveen, H.; KINGMA, R. F.

doi:10.1016/s0040-4039(00)81487-2

Cited by 56 publications

(17 citation statements)

References 13 publications

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“…In the presence of phenylacetylene, compound 7 can undergo a [1+2] cycloaddition followed by a second TMSCl elimination to yield the cycloadduct 4 a . The [1+2] cycloaddition of phosphenium cations and alkynes is well established, and provides a solid grounding as to why phosphirene sulfide ( 4 ) are the only products formed.…”

Section: Figurementioning

confidence: 99%

“…[31] Therefore we propose that using method(ii)(Scheme3,right) proceeds via the stepwise elimination of TMSCl, giving rise to ap hosphenium-like intermediate (7). In the presenceo fp henylacetylene, compound 7 can undergo a[ 1 + +2] cycloaddition followed by as econd TMSCl elimination to yield the cycloadduct 4a.T he [1+ +2] cycloaddition of phosphenium cations and alkynes is well established, [44] and providesasolid grounding as to why phosphirene sulfide (4) are the only products formed.…”

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confidence: 99%

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Addressing the Nature of Phosphinidene Sulfides via the Synthesis of P−S Heterocycles

Graham

Macdonald

Boyle

et al. 2017

Chemistry A European J

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The phosphorus-sulfur heterocycles 1,2-thiaphosphetenes and phosphirene sulfides have been prepared, and represent the first structurally characterized derivatives for either class of compound. These strained P-S ring systems are formed by the reaction of a phosphinidene sulfide and alkyne. Using an internal alkyne, only the 3-membered P , phosphirene sulfide was produced, whereas a terminal alkyne yielded a mixture of phosphirene sulfide and 1,2-thiaphosphetene (P ). Detailed computational analysis revealed that for numerous derivatives of alkynes, the corresponding 4-membered rings are always more stable than the 3-membered isomers. The electronic nature of "free" phosphinidene sulfides (R-P=S) is discussed based on computational results.

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Section: Figurementioning

confidence: 99%

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confidence: 99%

Addressing the Nature of Phosphinidene Sulfides via the Synthesis of P−S Heterocycles

Graham

Macdonald

Boyle

et al. 2017

Chemistry A European J

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“…The corresponding work has been summarized in two reviews [182,183]. A surprisingly simple synthesis of phosphirenes has also been devised (Scheme 23.68) [184,185].…”

Section: Three-membered Rings: Phosphiranes and Phosphirenesmentioning

confidence: 99%

Phosphorus Heterocycles

Mathey

2011

Modern Heterocyclic Chemistry

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Figure 23.1 The three isomers of the phosphole system (A-C) and the phospholide ion (D).2072j 23 Phosphorus Heterocycles shown with 1-alcoxyphospholes, which are relatively flat with a negligible delocalization [12]. Contrary to phospholes, the structure of phospholide ions reflects their high aromaticity. For example, the planar 2,3,4,5-tetramethylphospholide with Li(TMEDA) þ as the counterion displays the following parameters [13]: P-C, 1.715 A ; C¼C, 1.396 A ; CÀC, 1.424 A ;

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“…Subsequent thermolysis eventually led to the SCHEME 1 formation of the respective phospholes 4 [10] by a sequence of 1,1-carboboration steps [11,12]. At present, it is not clear whether these phosphirenium borates (1,3) are reactive intermediates on the way to the formation of the 1,1-carboboration products or if they are formed in a competing equilibrium situation.…”

Section: Introductionmentioning

confidence: 99%

Zwitterionic Phosphirenium Borates Derived from Bis(alkynyl)mesityl Phosphanes and Tris(pentafluorophenyl)borane

Möbus

Malessa

Frisch

et al. 2014

Heteroatom Chemistry

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From a series of bis(alkynyl)mesityl phosphanes 5, we prepared phosphirenium borate compounds 6 in high yields by reaction with B(C6F5)3 at room temperature. The zwitterionic compounds 6 are conveniently accessible and can be obtained with unique substitution patterns by this route. For two examples, we show the conversion of 6 to the respective 3‐borylated phosphole derivatives 7 through multiple 1,1‐carboboration reactions. In a useful one‐pot methodology, the phosphirenium borates 6 are converted to air‐stable 3‐arylated phospholes 8 by a sequential 1,1‐carboboration/ Suzuki–Miyaura type cross‐coupling reaction.

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Synthesis of phosphirenium salts

Cited by 56 publications

References 13 publications

Addressing the Nature of Phosphinidene Sulfides via the Synthesis of P−S Heterocycles

Addressing the Nature of Phosphinidene Sulfides via the Synthesis of P−S Heterocycles

Phosphorus Heterocycles

Zwitterionic Phosphirenium Borates Derived from Bis(alkynyl)mesityl Phosphanes and Tris(pentafluorophenyl)borane

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