A New Concept for the Efficient Synthesis of Chiral Phosphorus−Nitrogen−Carbon Cage Compounds

Hoffmann, Nils; Wismach, Catleen; Ernst, Ludger; Schiebel, Hans‐Martin; Jones, Peter G.; Streubel, Rainer

doi:10.1002/ejic.200200649

Cited by 8 publications

(3 citation statements)

References 25 publications

(27 reference statements)

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“…In contrast to this, 1,2λ 3 -azaphospholenes V − IX (Scheme ) are still elusive species, because of a significant lack of synthetic strategies for these ring systems. For example, there are only two short communications on complexes having a 1,2λ 3 -azaphosphol-4-ene ( V ), , some on 1,2λ 3 -azaphosphol-3-enes ( VI )either free or in a P-ligated fashionand on 1,2λ 3 -azaphosphol-3-enes ( VII ). , Very recently, the latter, chiral so-called Wilke's-azaphospholene, has received increased attention in catalysis. , …”

Section: Introductionmentioning

confidence: 99%

1,2-Azaphosphol-5-ene Complexes through Metal-Assisted Synthesis

et al. 2006

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Thermal ring opening of {[2-bis(trimethylsilyl)methyl-3-phenyl-2H-azaphosphirene-κP]pentacarbonyltungsten(0)} (1) in toluene in the presence of 1-piperidino carbonitrile (2) and various mono-and disubstituted alkenes, i.e., ethyl acrylate (4), E-stilbene (6), fumaronitrile (7), and maleic anhydride (10), was investigated. Special emphasis was placed on the dependence of the regio-and stereoselectivity of the transiently formed nitrilium phosphane-ylide complex 3 on the electronic properties of the alkenes. Three-component reaction of 1, 2, and 4 yielded regioselectively a 1:1 mixture of the diastereomeric 4-ethoxycarbonyl-substituted 1,2-azaphosphol-5-ene complexes 5a,b; the constitution of 5a was unambiguously established by single-crystal X-ray diffraction. Whereas E-stilbene (6) gave no reaction with complex 3, fumaronitrile (7) reacted with transient 3 to furnish the diastereomeric 1,2-azaphosphol-5-ene complexes 8a,b together with the 2H-1,3,2-diazaphosphole complex 9; the product ratio of 2:1:1 was determined by 31 P{ 1 H} NMR spectroscopy. Reaction of 1, 2, and maleic anhydride (10) resulted in a complicated product mixture, whereby the constitution of the spirocyclic complexes 11a,b (bearing a 1,3,2-oxazaphosphol-3-ene moiety) is based on their NMR data. Further examination showed that the C-O double bond system of 10 did not participate in a [3+2] cycloaddition reaction if the thermal decomposition of complex 1 was carried out in neat benzonitrile, thus showing the preference of the transiently formed C-phenylsubstituted nitrilium phosphane-ylide complex 12 for the C-C double bond of 6: In this case, the bicyclic complexes 13a,b were formed exclusively.

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Section: Introductionmentioning

confidence: 99%

1,2-Azaphosphol-5-ene Complexes through Metal-Assisted Synthesis

et al. 2006

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“…When the reaction was performed with Ph 3 P=NCN in dry toluene, the 1,2-azaphosphole complex 70 was formed in high yield (Scheme 21). 33,55…”

Section: Scheme 20mentioning

confidence: 99%

The synthesis of 1,2-azaphospholes, 1,2-azaphosphorines and 1,2-azaphosphepines

Hassanin¹,

Ali²,

Assiri³

et al. 2020

Arkivoc

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“…80 The Cp * -substituted 2H-1,2-azaphosphole complex 26 has been converted into the chiral phosphorus-nitrogen-carbon cage compound 27 by consecutive inter-and intra-molecular Diels-Alder reactions. 81 The reaction of the trilithium phosphazenate [{(thf) 2 Li} 3 (PhNH) 3 (PhN) 3 P 3 N 3 }] with trimethylaluminium has been shown to give the first mixed-metal phosphazenate complex [{(thf) 2 Li} 3 Me 2 Al{(PhNH) 2 (PhN) 4 P 3 N 3 }]. 82 The reaction of a trichloroiminophosphorane with a zirconaindane complex has led to metallaspirophosphanes such as 28.…”

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confidence: 99%

7 Nitrogen, phosphorus, arsenic, antimony and bismuth

Burrows

2004

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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Group 15 has generated fascinating chemistry in recent years, and 2003 was no exception. Highlights of the year included the preparation of an inorganic fullerenelike compound containing P 5 and P 4 Cu 2 rings, 1 an arsenic-nickel complex with a three-shell structure 2 and the isolation of the phosphorus oxide ozonide P 4 O 18 . 3 Details of all of these are included below. Nitrogen and phosphorus compounds have continued to be used extensively as ligands, though space limitations have precluded detailing the use of Group 15-containing compounds in this manner unless transformation of the ligand itself was involved or an unusual coordination mode was observed. As in previous years the summaries of each work cited are as concise as possible in order to maximise the range of chemistry described.

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A New Concept for the Efficient Synthesis of Chiral Phosphorus−Nitrogen−Carbon Cage Compounds

Cited by 8 publications

References 25 publications

1,2-Azaphosphol-5-ene Complexes through Metal-Assisted Synthesis

1,2-Azaphosphol-5-ene Complexes through Metal-Assisted Synthesis

The synthesis of 1,2-azaphospholes, 1,2-azaphosphorines and 1,2-azaphosphepines

7 Nitrogen, phosphorus, arsenic, antimony and bismuth

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