Ungewöhnlich koordinierte Phosphorverbindungen

Fuchs, Evelyn; Hermesdorf, M.; Schnurr, W.; Rösch, Wolfgang; Heydt, H.; Regitz, Manfred; Binger, Paul

doi:10.1016/0022-328x(88)80006-8

Cited by 48 publications

(15 citation statements)

References 32 publications

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“…; 70a, C,D6), 6=66.8-81.9 Despite the steric bulk of its substituents, the PC double bond of 70d is so reactive that it takes up a further mole of the dipole 69d to give the heterobicyclic compound 72.lS9l A corresponding reaction of 3d with 4-chlorophenylnitrile oxide is also The trapping reaction of HC=P 4 with 69a also is a 1 :2 addition. [22] …”

Section: H-124-diazaphospholesmentioning

confidence: 97%

Phosphaalkynes—Syntheses, Reactions, Coordination Behavior [New Synthetic Methods (73)]

Regitz

Binger

1988

Angew. Chem. Int. Ed. Engl.

232

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Methods (73)Organophosphorus compounds have been applied in two ways in chemical synthesis. They can either be used as a reagent in a step of the synthesis (for example, in the Wittig reaction) or they can be incorporated directly into the target molecule. This second application, in particular, has expanded greatly in the last few years with the preparation of low-coordination phosphorus compounds. These include the phosphaalkynes, which are of great interest to organic and inorganic chemists. Phosphaalkynes have been employed in the synthesis of heterocyclic compounds, phosphaarenes and their valence isomers, and polycyclic compounds. Further applications have been the use of phosphaalkynes as new ligand systems in complex chemistry and their cyclooligomerization with organometallic reagents. While the chemical properties of phosphaalkynes have little in common with those of nitriles, they are in many ways very similar to those of the isoelectronic acetylenes.

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Section: H-124-diazaphospholesmentioning

confidence: 97%

Phosphaalkynes—Syntheses, Reactions, Coordination Behavior [New Synthetic Methods (73)]

Regitz

Binger

1988

Angew. Chem. Int. Ed. Engl.

232

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“…Zum einen liefern 1,3-dipolare Cycloadditionen von Acyldiazoalkanen mit geeignet substituierten Phosphaalkenen wie etwa Me 3-SiPϭC(R 1 )OSiMe 3 oder ClPϭC(R 1 )SiMe 3 gewöhnlich 1,2,4-Diazaphosphole und nicht die hier erhaltenen 1,2,3-Isomere [11]. Diazoalkane addieren sich auch regiospezifisch unter P-C-Verknüpfung an Phosphaalkine R 2 CϵP (R 2 ϭ Neopentyl, iPr, tBu) [12]. Die regioisomeren 1,2,3-Diazaphosphole entstehen jedoch als Nebenprodukte bei der Cycloaddition von N 2 ϭCH-CO 2 tBu an HCϵP [12] oder von CF 3 CHϭN 2 und N 2 ϭCHCO 2 Me an iPr 2 N-CϵP [13].…”

Section: Ergebnisse Und Diskussionunclassified

“…Diazoalkane addieren sich auch regiospezifisch unter P-C-Verknüpfung an Phosphaalkine R 2 CϵP (R 2 ϭ Neopentyl, iPr, tBu) [12]. Die regioisomeren 1,2,3-Diazaphosphole entstehen jedoch als Nebenprodukte bei der Cycloaddition von N 2 ϭCH-CO 2 tBu an HCϵP [12] oder von CF 3 CHϭN 2 und N 2 ϭCHCO 2 Me an iPr 2 N-CϵP [13].…”

Section: Ergebnisse Und Diskussionunclassified

Azodicarbonsäureester und Diazoessigester als Reaktionspartner des Ferriophosphaalkens [Cp*(CO)2FeP=C(Ph)NMe2]

Weber

Kleinebekel

Stammler

et al. 2002

Z. anorg. allg. Chem.

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Bei der Redaktion eingegangen am 5. Dezember 2001. Inhaltsübersicht. Die Reaktion äquimolarer Mengen des Ferriophosphaalkens [Cp*(CO) 2 FePϭC(Ph)NMe 2 ] (1) und Azodicarbonsäurediethylester liefert den Komplex (C 5 Me 4 CH 2 )(CO) 2 -FeP T{CH(Ph)NMe 2 }N(CO 2 Et)NϭC(CO 2 Et)O U (3) als Ergebnis einer cheletropen [1ϩ4]-Cycloaddition mit nachfolgender Umprotonierung. Die Diazoessigester N 2 ϭCHCO 2 R (8a:RϭtBu; 8b:Et) rea-Abstract. Reaction of equimolar amounts of the ferriophosphaalkene [Cp*(CO) 2 FePϭC(Ph)NMe 2 ] (1) and diethyl azodicarboxylate afforded the complex [(C 5 Me 4 CH 2 )(CO) 2 FeP T{CH(Ph)NMe 2 }N-(CO 2 Et)NϭC(CO 2 Et)O U (3) as the result of a cheletropic [1ϩ4] cycloaddition with subsequent transprotonation. The diazoacetates N 2 ϭCHCO 2 R (8a:ϭtBu; 8b:Et) and 1 gave rise to the formation of the N-metallated 1,2,3-diazaphospholes

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“…In fact only the reaction of phosphaacetylene with t-butyl diazoacetate is known to afford both regioisomers. 7 While the rather low Ž . lying lowest unoccupied molecular orbital LUMO of phosphaacetylene 8 gives rise to a low energy transition state, the nearly equal molecular orbital Ž .…”

Section: Introduction Ycloaddition Reactions 1 Play An Importantmentioning

confidence: 97%

“…Ž . here of diazomethane 1 and phosphaacetylene 2 the reaction runs regiospecific 7 and proceeds even at rather low temperatures. The latter observation indicates that the activation barrier of the reaction is quite small.…”

Section: Introduction Ycloaddition Reactions 1 Play An Importantmentioning

confidence: 99%

Regioselectivity in cycloaddition reaction between phosphaacetylene and diazomethane: Anab initio study

Nyulászi¹,

Várnai²,

Eisfeld

et al. 1997

J. Comput. Chem.

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Ungewöhnlich koordinierte Phosphorverbindungen

Cited by 48 publications

References 32 publications

Phosphaalkynes—Syntheses, Reactions, Coordination Behavior [New Synthetic Methods (73)]

Phosphaalkynes—Syntheses, Reactions, Coordination Behavior [New Synthetic Methods (73)]

Azodicarbonsäureester und Diazoessigester als Reaktionspartner des Ferriophosphaalkens [Cp*(CO)2FeP=C(Ph)NMe2]

Regioselectivity in cycloaddition reaction between phosphaacetylene and diazomethane: Anab initio study

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