Six-membered Rings with Two or More Heteroatoms with at least One Phosphorus Atom

Maerkl, G.; Kreitmeier, Peter

doi:10.1016/b978-008043952-5/50014-0

Cited by 6 publications

(1 citation statement)

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“…After having access to a good number of differently substituted derivatives of these four classes of 2-phosphaindolizines, we were motivated to explore their reactivity as they apparently have many active functionalities. In view of the earlier reported results of the Diels-Alders (DA) reaction across the >C=Pfunctionality in phosphaalkenes [6], phosphaketenes [6], heterophospholes [7], phosphinines [8], and azaphosphinines [9] (a recent review incorporates all these classes [10]), we investigated DA reactions across the >C=P-or -N=P-functionality present in these compounds. During this, we found that these compounds exhibited quite different dienophilic reactivities towards 2,3-dimethyl-1,3-butadiene (DMB).…”

Section: Introductionmentioning

confidence: 99%

Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

Beig¹,

Peswani²,

Bansal³

2022

Beilstein J. Org. Chem.

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The >C=P– or –N=P– functionality in 1,3-azaphospholo[1,5-a]pyridine, named as 2-phosphaindolizine and its 1- and 3-aza derivatives act as dienophiles and undergo Diels–Alder reactions with 1,3-dienes. However, the dienophilic reactivity is affected by the nature of the substituent groups on the two sides of the σ2,λ3-P atom and also by the presence of more nitrogen atom(s) in the five-membered ring. The conceptual density functional theory (DFT) calculations have been used in recent years to predict the reactivity of organic molecules in reactions. We calculated global hardness (η), global softness (S), electronic chemical potential (μ), electrophilicity (ω), and nucleophilicity (N) indices of four classes of 2-phosphaindolizines, on the basis of which their observed relative dienophilic reactivities could be rationalized. Besides, the Fukui functions of the carbon/nitrogen and phosphorus atoms of the >C=P– and –N=P– functionalities were also computed which revealed their hard electrophilic character and accorded well with the dienophilic reactivities observed experimentally. Furthermore, energies and symmetries of the lowest unoccupied molecular orbitals (LUMO) of 2-phosphaindolizines were found to be in conformity with their dienophilic reactivities.

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Section: Introductionmentioning

confidence: 99%

Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

Beig¹,

Peswani²,

Bansal³

2022

Beilstein J. Org. Chem.

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A Phosphorus Analogue of p‐Quinodimethane with a Planar P₄ Ring: A Metal‐Free Diphosphorus Source

Rottschäfer

Neumann

Stammler

et al. 2019

Chemistry A European J

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Para-quinodimethane (pQDM) is af undamental structural component in many p-conjugated organic molecules andm aterials. The incorporation of phosphorus atom into p-conjugated frameworks offersu nique opportunitiesf or controlling the properties of derived species. A phosphorus analogueo fp-quinodimethane (pQDM), (IPrC) 2 P 4 [5,I Pr = C{N(Ar)CH 2 } 2 ;A r= 2,6-iPr 2 C 6 H 3 ]f eaturinga planar P 4 ring, was readily accessible by KC 8 -reduction of (IPrC)(PCl 2 ) 2 (2). Base-mediatedC ÀHf unctionalizationo f IPrCH 2 (1)w ith PCl 3 afforded 2.T he formation of 5 was expected to occur through ad imerization of the transient 3H-diphosphirene (IPrC)P 2 (4), which was theoretically suggested to have an intermediate diradical character.C ompound 5 underwentp hoto-induced ring-contraction reaction to form the singlet diradicaloid (IPrCP) 2 VI and white phosphorus (P 4 ). Thef ormationo fa nd VI andP 4 suggested the formald iphosphorus( P 2 )e limination from 5.

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ChemInform Abstract: Six‐membered Rings with Two or More Heteroatoms with at Least One Phosphorus Atom

Maerkl

Kreitmeier

2002

ChemInform

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Six-membered Rings with Two or More Heteroatoms with at least One Phosphorus Atom

Cited by 6 publications

References 296 publications

Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

A Phosphorus Analogue of p‐Quinodimethane with a Planar P₄ Ring: A Metal‐Free Diphosphorus Source

ChemInform Abstract: Six‐membered Rings with Two or More Heteroatoms with at Least One Phosphorus Atom

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Six-membered Rings with Two or More Heteroatoms with at least One Phosphorus Atom

Cited by 6 publications

References 296 publications

Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

A Phosphorus Analogue of p‐Quinodimethane with a Planar P4 Ring: A Metal‐Free Diphosphorus Source

ChemInform Abstract: Six‐membered Rings with Two or More Heteroatoms with at Least One Phosphorus Atom

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A Phosphorus Analogue of p‐Quinodimethane with a Planar P₄ Ring: A Metal‐Free Diphosphorus Source