Phosphazenes. 2. Synthesis of ketone- and enol-substituted cyclotriphosphazenes

Harris, Paul J.; Schwalke, Michael A.; Liu, Vicky; Fisher, Bernie L.

doi:10.1021/ic00154a024

Cited by 20 publications

(8 citation statements)

References 3 publications

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“…Mass and NMR ( and31 P) spectral data of the respective chromatographically isolated pure compounds (Tables 1 and 2) Both reactions were found to yield the respective monooxy-[oxo(alkyl (2) or cycloalkyl (5))ene]-substituted derivatives, respectively, as the major products (~50% of the theoretical yield). Small amounts of the corresponding isomeric gem (3,6) and non-gem (4,7) disubstituted derivatives have also been isolated, the respective non-gem isomers being always formed preferably (see Experimental Section). Non-geminal regioselectivity is typical for substitution reactions of halogenophosphazenes with oxyanions.12 31P NMR spectra of all the obtained derivatives represent spin systems of A2B type, with the chemical shifts vp, coupling constants Jp.p and the respective intensity ratios [A]/[B] consistent with the assumed structures (2-7).…”

Section: Resultsmentioning

confidence: 99%

New Heterofunctional Cyclophosphazenes with Carbonyl and Double Bond Functions

Drozd¹,

Brandt²,

Kupka³

1994

Inorg. Chem.

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Section: Resultsmentioning

confidence: 99%

New Heterofunctional Cyclophosphazenes with Carbonyl and Double Bond Functions

Drozd¹,

Brandt²,

Kupka³

1994

Inorg. Chem.

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“…The monosubstituted derivatives were isolated and characterized in all cases, as well as several di-, tri-, tetra-substituted derivatives, and the hexa-substituted derivatives, but not the penta-substituted ones. Other early examples of reactivity concerned enolate anions of acetaldehyde, acetone, and acetophenone, using lithium derivatives [ 7 ], methylsilane and methylsiloxane, using Grignard reagents [ 8 ], and phenols, using the sodium salt [ 9 ]. In the latter case, the penta-substituted derivative was easily obtained, and frequently used.…”

Section: Introductionmentioning

confidence: 99%

AB5 Derivatives of Cyclotriphosphazene for the Synthesis of Dendrons and Their Applications

et al. 2021

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AB5 compounds issued from the reactivity of hexachlorocyclotriphosphazene are relatively easy to obtain using two ways: either first the reaction of one chloride with one reagent, followed by the reaction of the five remaining Cl with another reagent, or first the reaction of five chlorides with one reagent, followed by the reaction of the single remaining Cl with another reagent. This particular property led to the use of such compounds as core for the synthesis of dendrons (dendritic wedges), using the five functions for growing the dendritic branches. The single function can be used for the synthesis of diverse types of dendrimers (onion peel, dumbbell-shape, Janus), for covalent or non-covalent grafting to solid surfaces, providing nanomaterials, for grafting a fluorophore, especially for studying biological mechanisms, or for self-associations to get micelles. All these properties are reviewed in this paper.

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“…In the synthesis of alkyl-and aryl-substituted phosphazenes, a halophosphazene is reacted with an organolithium or Grignard reagent [28][29][30][31][32][33]. Although there are many publications about cyclic, polymeric alkyl-, or arylphosphazenes [34][35][36][37][38][39][40], the synthesis of linear alkyl-substituted phosphazenes has been performed with only limited success [41,42].…”

Section: Introductionmentioning

confidence: 99%