Bicyclic phosphanes: synthesis, stereochemistry, and conformation

Bonningue, Corine; Houalla, D.; Sanchez, M.; Wolf, Robert; Osman, F. H.

doi:10.1039/p29810000019

Cited by 24 publications

(14 citation statements)

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“…This dimerization of the ADPO fragment is surprising because it is not characteristic of ADPO chemistry. Saturated analogs of ADPO have been observed to dimerize in this fashion [29,30] without the need for a metal catalyst (Scheme 2), but ADPO has resisted undergoing the analogous reaction.…”

Section: Adpo-fe( Co)-tsmentioning

confidence: 99%

The syntheses and structures of iron carbonyl adducts of tricoordinated hypervalent phosphorus compounds

Arduengo

Lattman

Dixon

et al. 1991

Heteroatom Chemistry

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Section: Adpo-fe( Co)-tsmentioning

confidence: 99%

The syntheses and structures of iron carbonyl adducts of tricoordinated hypervalent phosphorus compounds

Arduengo

Lattman

Dixon

et al. 1991

Heteroatom Chemistry

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“…[2] Amongt hese phosphorush eterocycles, it has been reportedt hat monophosphapentalenes Ia-c, II,a nd diphosphapentalenes III-VI composed of two fused five-membered rings display unique chemical behaviors( Figure 1a). [3,4] By incorporation of the phosphorus atom into the bridgehead in ab icyclic skeleton, the s 3 -P framework significantly deviates from typical C 3v threefold symmetry,w hich leads to an on-canonicalb onding situation as well as reactivity.M onophosphapentalene Ia readily undergoes oxidative addition to the NÀHb ond of amines and the OÀH bonds of alcohol. [5] Radosevich et al demonstrated that compound Ib,w hich features au nique planar structure, is able to activate ammonia-borane as well as ammonia, and the former provedu seful in catalytic transfer hydrogenation of azobenzene.…”

Section: Introductionmentioning

confidence: 99%

Reactivity Studies on a Diazadiphosphapentalene

Cui

Ganguly

et al. 2016

Chemistry A European J

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The reactivity of diazadiphosphapentalene 1 towards various substrates was investigated. Reaction of 1 with ammonia-borane resulted in transfer hydrogenolysis concomitantly with the cleavage of a P-N bond. By treatment of 1 with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), oxidation took place at one of the phosphorus atoms of 1, and a P(V) /P(III) mixed-valence derivative was isolated. At the same time, it was demonstrated that only one of the phosphorus atoms in 1 behaves as an electron donor for electrophiles and Lewis acids. The former afforded an intramolecularly coordinated phosphine-phosphenium species, whereas the latter demonstrates the ligand property of 1. UV irradiation induced rearrangement of 1 into another example of another diazadiphosphapentalene.

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“…or on PCl^ in the presence of a base, the synthesis is rather delicate owing to the secondary products which are formed. The difficulties encountered in the preparation of 7_ have been described (3) .…”

Section: Me Mementioning

confidence: 99%

Synthesis and Chemical Behavior of Some Bicyclophosphanes

Bonningue¹,

Diallo²,

Houalla³

et al. 1981

ACS Symposium Series

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Although numerous acyclic amidophosphites of type 1, 2 and 3 have been described very early, until recently no bicyclic compound like 4 was known.In a note published in 1977 (1), we have described the 2,8-dioxa-5-aza-1-phospha III bicyclo[3.3.0]octanes 4 and 5. In spite of their structural simplicity, they were, to our knowledge, the first phosphorus derivatives of this kind ever described, although the arsenic homologue of 4 has been known since 1970 (2).Such compounds were not obtained sooner due to two difficulties we met during our approach. (i) First the compounds tend to oligomerize quite easily, however the presence of substituents slows down the phenomenon. (ii) The second difficulty comes from the fact that these compounds can add any molecule with a mobile hydrogen (ROH, R 2 NH etc...) leading mainly to phosphoranes with a P-H bond 6 (X = RO-, R 2 N-).These two observations show that double cyclisation confers on the bicyclic phosphanes particular properties and we were prompted to continue our research in this field.We have described recentlyfour new bicyclic phosphanes 7, 8 9 (3) and 10 (4) while three interesting articles have been devoted to 10 (5), 4 (6) and 11 (7).

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Bicyclic phosphanes: synthesis, stereochemistry, and conformation

Cited by 24 publications

References 0 publications

The syntheses and structures of iron carbonyl adducts of tricoordinated hypervalent phosphorus compounds

The syntheses and structures of iron carbonyl adducts of tricoordinated hypervalent phosphorus compounds

Reactivity Studies on a Diazadiphosphapentalene

Synthesis and Chemical Behavior of Some Bicyclophosphanes

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