Template synthesis of 9-membered triphospha-macrocycles with rigid o-phenylene backbone functions

Edwards, Peter G.; Whatton, Mark L.

doi:10.1039/b511502g

Cited by 25 publications

(5 citation statements)

References 13 publications

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“…Use of a metal template, however, allows such ligands to be prepared in fewer steps and overall higher yields than might otherwise be possible. For example, Edwards and co-workers have used coupling reactions between coordinated primary diphosphines and vinylphosphines to prepare cyclic triphosphines with 9−12 membered rings . Stelzer and co-workers have used a related approach to prepare cyclic tetraphosphines, and also employed the reaction between coordinated secondary diphosphines and diketones to prepare similar products .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Electrochemistry of a Series of Iron(II) Complexes Containing Self-Assembled 1,5-Diaza-3,7-diphosphabicyclo[3.3.1]nonane Ligands

et al. 2009

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The reaction between PPh(CH(2)OH)(2), iron(II) sulfate, ammonium sulfate, and formaldehyde in aqueous solution gives the iron(II) complex [Fe(kappa(2)-O(2)SO(2))L(2)] (1), where L is the bidentate phosphine ligand 3,7-diphenyl-1,5-diaza-3,7-diphosphabicyclo[3.3.1]nonane. During the course of the reaction, the ligand L self-assembles on the metal center. The reaction between PPh(CH(2)OH)(2), iron(II) chloride, ammonium chloride, and formaldehyde under similar conditions gives cis-[FeCl(2)L(2)] (cis-2). The complex cis-2 is converted into trans-2 in Et(2)O, whereas in water it is converted into cis-[Fe(OH(2))(2)L(2)](2+), though both of these interconversions are reversible. The chloro ligands in cis-2 are readily displaced by reaction with thiocyanate, azide, and carbonate to give cis- and trans-[Fe(NCS)(2)L(2)] (cis- and trans-3), cis- and trans-[Fe(N(3))(2)L(2)] (cis- and trans-4), and [Fe(kappa(2)-O(2)CO)L(2)] (5), respectively. The complex cis-2 reacts with CO in water to give trans-[FeCl(CO)L(2)]Cl (trans-6), whereas trans-2 reacts with CO in diethyl ether to give cis-[FeCl(CO)L(2)]Cl (cis-6), though cis-6 isomerizes in water to form trans-6. The reaction of cis-2 with sodium borohydride gives the hydride chloride complex trans-[FeCl(H)L(2)] (7). Electrochemical studies have been undertaken on complexes 1, cis-2, and 7. These reveal reversible oxidations for cis-2 and 7, with the latter giving rise to an unusual 17-electron iron(III) hydride chloride complex. Crystal structures have been obtained for 1, trans-2, trans-3, 5, and 7.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Electrochemistry of a Series of Iron(II) Complexes Containing Self-Assembled 1,5-Diaza-3,7-diphosphabicyclo[3.3.1]nonane Ligands

et al. 2009

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“…Template synthesis 17 is a particularly attractive and efficient method for the synthesis of phosphorus-donor ligands. [18][19][20][21][22][23][24][25][26][27][28][29][30] * Author to whom correspondence should be addressed. E-mail: rmorris@chem.utoronto.ca.…”

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confidence: 99%

“…This method allows the combinatorial synthesis of a large number of related catalyst structures to aid the search for the ones displaying optimum activity and selectivity. Template synthesis is a particularly attractive and efficient method for the synthesis of phosphorus-donor ligands. – …”

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confidence: 99%

Template Syntheses of Iron(II) Complexes Containing Chiral P−N−N−P and P−N−N Ligands

et al. 2008

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“…No metal complexes of the ligand were reported but the methyl iodide salt [9] The majority of the reports related to [9]aneP 3 type cyclononane ligands has arisen from one group, much of the chemistry utilising the activated, electrophilic ortho-fluorophenyl substituent on a neighbouring pnictide donor [288][289][290][291][292][293][294][295][296][297][298][299].…”

Section: Synthesismentioning

confidence: 99%

Cyclononanes: The extensive chemistry of fundamentally simple ligands

Gahan

2016

Coordination Chemistry Reviews

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The cyclononane ligands are fundamental examples of the macrocyclic ligand. With three donor atoms in a nine-membered ring they represent the simplest of the macrocyclic class. However, this simplicity is deceptive, for within this class the variations are extensive and perhaps hitherto unrecognized. As well as the relatively familiar 1,4,7-triaza-([9]aneN 3) and 1,4,7-trithia-([9]aneS 3) cyclononanes whole families of cyclononane ligands are known with thioether/nitrogen, nitrogen/oxygen, selenium, tellurium as well as phosphorus and arsenic donors. The chemistry of some of these ligands, for example [9]aneN 2 S, [9]aneNS 2 and [9]aneN 2 O has been reported extensively, and some examples have simply been reported as having been synthesised (for example [9]aneO 2 S and [9]aneO 2 Se) with little other information. This review attempts to introduce the extensive chemistry of what are fundamentally the simplest examples of macrocyclic ligands. 1. Highlights Review of current trends in cyclononane chemistry Diversity of donor groups and transition metal chemistry complexes which arise Significant new synthetic chemistry Significant advances in the applications of cyclononane ligands

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Template synthesis of 9-membered triphospha-macrocycles with rigid o-phenylene backbone functions

Cited by 25 publications

References 13 publications

Synthesis, Characterization, and Electrochemistry of a Series of Iron(II) Complexes Containing Self-Assembled 1,5-Diaza-3,7-diphosphabicyclo[3.3.1]nonane Ligands

Synthesis, Characterization, and Electrochemistry of a Series of Iron(II) Complexes Containing Self-Assembled 1,5-Diaza-3,7-diphosphabicyclo[3.3.1]nonane Ligands

Template Syntheses of Iron(II) Complexes Containing Chiral P−N−N−P and P−N−N Ligands

Cyclononanes: The extensive chemistry of fundamentally simple ligands

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