Photochemical reactions of phosphaalkenes

Meriem, A.; Majoral, Jean‐Pierre; Revel, M.; Navech, Jacques

doi:10.1016/s0040-4039(00)81820-1

Cited by 55 publications

(10 citation statements)

References 16 publications

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“…No evidence of any reaction at either ambient or elevated temperatures was detected based on in situ 11 B{ 1 H} and 31 P{ 1 H} NMR spectroscopy. As it is well established that UV irradiation is capable of inducing PP bond cleavage in the photolytic conversion of white phosphorus into red phosphorus,16 we were attracted to the report of Navech and co‐workers speculating that the photolysis of [PPh] 5 formed phosphinidene fragments 17. The experiment conducted in non‐deoxygenated methanol produced H 2 PPh, (CH 3 O) 2 PPh, and HP(O)Ph(OCH 3 ), products believed to originate from the quenching of the photolytically generated phosphinidene fragments.…”

Section: Methodsmentioning

confidence: 99%

1,2‐Phosphaborines: Hybrid Inorganic/Organic P–B Analogues of Benzene

et al. 2015

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Photolysis of the cyclic phosphine oligomer [PPh]5 in the presence of pentaarylboroles leads to the formation of 1,2-phosphaborines by the formal insertion of a phenylphosphinidene fragment into the endocyclic CB bond. The solid-state structure features a virtually planar central ring with bond lengths indicating significant delocalization. Appreciable ring current in the 1,2-phosphaborine core, detected in nuclear independent chemical shift (NICS) calculations, are consistent with aromatic character. These products are the first reported 1,2-BPC4 conjugated heterocycles and open a new avenue for BP as a valence isoelectronic substitute for CC in arene systems.

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Section: Methodsmentioning

confidence: 99%

1,2‐Phosphaborines: Hybrid Inorganic/Organic P–B Analogues of Benzene

et al. 2015

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“…(14), (15)]. [8,46] Classical reactions of olefins, such as catalytic hydrogenation [47] and epoxidation [48] can only be achieved after [49] whereas hydrozirconation [50] leads to the P À H products [Eqs. (18) [2] Only some of the most significant cases will be treated here.…”

Section: Reactivitymentioning

confidence: 99%

Phospha‐Organic Chemistry: Panorama and Perspectives

2003

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Since the beginning of the seventies, organophosphorus chemistry has been completely rejuvenated by the discovery of stable derivatives in which phosphorus has the coordination numbers one or two. The chemistry of these compounds mimics the chemistry of their all-carbon analogues. In this Review article this analogy is discussed for the phosphorus counterparts of alkenes, alkynes, and carbenes. In each case, the synthesis, reactivity, and coordination modes are briefly examined. Some special electronic configurations are also discussed, which include one-electron Pbond;P bonds, strained bonds, and aromatic systems. To conclude, some potential applications of this chemistry in the areas of molecular materials and homogeneous catalysis are presented.

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“…As a matter of fact the polarity of this bond could be reversed by dialkylamino-substituents on the carbon side [4] .The regioselectivity by the addition of a polar reagent at the P C -bond can also be controlled by the type of substituents at the bond. Examples of proton addition to the different sides of P C bonds, as well as hydride addition to the different sides upon variation of the substituent, are known [5,6]. This kind of tunability is of great interest in catalytic chemistry, where retaining the same metal with a variation of sterical or electronic factors around the ligand could result in the appearance of new technologies [7].…”

Section: Introductionmentioning

confidence: 99%