New polyphosphorus ligands: addition reactions of 1,1-bisdiphenylphosphinoethene

Bookham, Jonathan L.; McFarlane, William; Colquhoun, Ian J.

doi:10.1039/c39860001041

Cited by 37 publications

(22 citation statements)

References 3 publications

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“…Co-ordination of phosphorus also results in an algebraic decrease in 2J(31P-1 3C), and this is consistent with values close to zero for 2J(PA'3c,) for (4). This coupling has similar values for (5) and ( 7) also, suggesting that for the ligands (6) and (3) it would be similar to that for (1). The other nominally two-bond phosphorus-carbon couplings of the backbone could also involve a metal-mediated three-bond pathway, although the absence of a strong dependence upon the particular metal atom suggests that this may not be an important factor.…”

Section: Ph2mentioning

confidence: 58%

Addition reactions and rearrangements of 2,3-bis(diphenylphosphino)propene and its complexes with Group 6 metal carbonyls: routes to complexes of 1,2,3-tris(diphenylphosphino)propane

Bookham¹,

McFarlane²

1990

J. Chem. Soc., Dalton Trans.

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The preparation of 2,3bis(diphenylphosphino)propene (1 ) and its Group 6 metal tetracarbonyl complexes are described. The attempted base-catalysed addition of PR,H to (1 ) results in rearrangement to trans-I ,2-bis(diphenylphosphino)propene ( 2 ) instead of the expected triphosphine. Under the same conditions the Group 6 metal carbonyl complexes of (1) can rearrange to complexes of the cis isomer of (2), but may also undergo the addition reaction to yield M (CO), complexes of the new ligand 1,2,3-tris(diphenyIphosphino)propane by adjustment of the reaction conditions. These on heating yield the corresponding M (CO), complexes. Proton, I3C, and ,'P n.m.r. spectral parameters of the new compounds are presented and are discussed in terms of metal-and backbone-mediated contributions and co-ordination chemical shifts.

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Section: Ph2mentioning

confidence: 58%

Addition reactions and rearrangements of 2,3-bis(diphenylphosphino)propene and its complexes with Group 6 metal carbonyls: routes to complexes of 1,2,3-tris(diphenylphosphino)propane

Bookham¹,

McFarlane²

1990

J. Chem. Soc., Dalton Trans.

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“…60) [142]. Formation of dppe was also observed after photolysis of a mixture of DPVP and Cr(CO) 6 or Mo(CO) 6 [143].…”

mentioning

confidence: 71%

“…(eq. 5, 6) [5,6]. Fluorinated diphenylphosphinoethane (dppe) derivatives 20 were also prepared using this methodology [7][8][9], as well as N, P, P and N, P, P, P tridentate and tetradentate ligands 21 [10].…”

Section: Bis- Tris- and Tetradentate Phosphinesmentioning

confidence: 99%

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

Julienne¹,

Toulgoat²,

Delacroix

et al. 2010

COC

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Alkenylphosphines are compounds of great interest in view of their structures. The most interesting feature is the carboncarbon double bond, which is directly linked to the phosphorus atom. Nucleophilic addition or cycloaddition reactions can take place at this unsaturation, which can also be used as a coordinating part in the presence of a metal. Thus, alkenylphosphines have found numerous applications in various fields of chemistry. They are useful intermediates in organic synthesis: numerous studies are devoted to their transformation into bidentate ligands, to their use as precursors for dendrimer and polymer chemistry or as ligand for homogeneous catalysis. Due to the presence of both the phosphorus atom and the carbon-carbon double bond, they are also of great interest in coordination chemistry and their different bonding modes have been largely documented. Moreover, after complexation to transition metal, a great amount of work has been carried out on their reactivity in cycloaddition reactions, as well as in functionalization of the carbon-carbon double bond and other miscellaneous reactions. These main applications will be reviewed hereafter.

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“…4, 5) [10,11] and for that of 1,2-bis(diarylphosphino)ethane 18, having electron withdrawing substituents on the aryl group (eq. 6) [12].…”

Section: Hydrophosphination Under Basic Conditionsmentioning

confidence: 99%

Hydrophosphination of Unactivated Alkenes, Dienes and Alkynes: A Versatile and Valuable Approach for the Synthesis of Phosphines

Delacroix

Gaumont

2005

COC

142

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The last years have seen many advances in the field of organometallic catalysis. Motivating much of the work has been the potential for discovering new catalytic reactions, which can be used for the synthesis of bulky chemicals and fine chemical intermediates. Since the efficiency and the selectivity of the catalyst mainly rely on the structure of the ligand, there is a great interest in the design and the synthesis of new ligands (amines, aminoalcohols, thioether, phosphines etc). From all of them, phosphine derivatives are the most widely used with transition metal catalysts. Different approaches have allowed to prepare phosphine derivatives: nucleophilic substitution of a P-chloro derivative, nucleophilic substitution using metal phosphide, C-P cross coupling etc. A greener way to phosphines is the addition of a P-H bond to a multiple bond since no atom loss is observed (atom economy concept). These reactions are mainly carried out in the presence of radical initiators or under basic conditions. Acidic and neutral media were also proposed. A few recent examples reported the use of a metal activation. This review is designed to remember some of the early aspects of hydrophosphination reactions using phosphines, protected or not, and unactivated or slightly activated alkenes, dienes and alkynes and to focus on the more promising results obtained in this field for the last 15 years. The reactions involving pentavalent phosphorus derivatives (phosphine-oxide, thiophosphines, phosphonate and phosphate derivatives etc.) are not concerned b y this chapter.

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New polyphosphorus ligands: addition reactions of 1,1-bisdiphenylphosphinoethene

Cited by 37 publications

References 3 publications

Addition reactions and rearrangements of 2,3-bis(diphenylphosphino)propene and its complexes with Group 6 metal carbonyls: routes to complexes of 1,2,3-tris(diphenylphosphino)propane

Addition reactions and rearrangements of 2,3-bis(diphenylphosphino)propene and its complexes with Group 6 metal carbonyls: routes to complexes of 1,2,3-tris(diphenylphosphino)propane

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

Hydrophosphination of Unactivated Alkenes, Dienes and Alkynes: A Versatile and Valuable Approach for the Synthesis of Phosphines

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