Onium Salt Catalyzed Preparation of Isocyanurates (Applications of Phase Transfer Catalysis, Part 28 [1])

Broda, W.; Dehmlow, Eckehard V.; Schulz, Hans‐Joachim

doi:10.1002/ijch.198500098

Cited by 9 publications

(1 citation statement)

References 12 publications

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“…[20] Moreover, their activity as catalysts in this reaction has been shown to be strongly influenced by the nature of the associated cation. [21] However, this anionicoligomerization process would not ultimately lead to the cyclotrimer 1, but to the palladacycle 4a due to the presence of the second acetate ligand on the nearby Pd(II) center. Indeed, the final steps would involve an intramolecular rearrangement taking place by elimination of acetic anhydride and carbon dioxide to form the metallacyclic core by ring closure.…”

Section: Scheme 4 Reaction Mechanism Proposed For the Formation Of 4mentioning

confidence: 99%

Formation of six-membered palladacycles from phenanthroline Pd(II) bisacetate precursors and phenylisocyanate

Moulin

Pellerin

Toupet

et al. 2014

Comptes Rendus. Chimie

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Synthesis and characterization of 5a-d. CCDC-221834 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via: www.ccdc.cam.ac.uk/data_request.cif.International audiencePhenylisocyanate reacts with palladium(II) bis-acetate phenanthroline complexes to give six-membered palladacycles in nearly quantitative yields. In this new reaction, the acetate ligands act as decarbonylating agents toward the isocyanate functionality by possibly forming the isolated palladacycles via an intramolecular rearrangement

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Section: Scheme 4 Reaction Mechanism Proposed For the Formation Of 4mentioning

confidence: 99%

Formation of six-membered palladacycles from phenanthroline Pd(II) bisacetate precursors and phenylisocyanate

Moulin

Pellerin

Toupet

et al. 2014

Comptes Rendus. Chimie

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[P(MeNCH₂CH₂) ₃N], ein effizienter Katalysator für die Umwandlung von Isocyanaten in Isocyanurate

Tang

Verkade

1993

Angewandte Chemie

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Auf die ungewöhnlich starke Lewis‐Basizität des P‐Atoms und auf die Fähigkeit zu unterschiedlich starken transanularen P‐N‐Wechselwirkungen ist die hohe katalytische Aktivität von [P(MeNCH2CH2) 3N] in der Titelreaktion zurückzuführen. So bildet sich, wie rechts angedeutet, in 3 min Triphenylisocyanurat (Ar = C6H5) in 97% Ausbeute und in 8 min Tri‐para‐methoxyphenylisocyanurat (Ar = 4‐MeOC6H4) in 99% Ausbeute.

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[P(MeNCH₂CH₂)₃N] as a Superior Catalyst for the Conversion of Isocyanates to Isocyanurates

Tang

Verkade

1993

Angew. Chem. Int. Ed. Engl.

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The unusually strong Lewis basicity of the P atom and the ability to form transannular PN interactions of various strengths account for the high catalytic activity of [P(MeNCH2CH2)3N] in the title reaction, a key step of which is shown on the right. Thus a 97% yield of triphenyl isocyanurate (Ar = C6H5) was obtained in 3 min, and a 99% yield of tri‐para‐methoxyphenyl isocyanurate (Ar = 4‐MeOC6H4) in 8 min.

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Onium Salt Catalyzed Preparation of Isocyanurates (Applications of Phase Transfer Catalysis, Part 28 [1])

Abstract: Abstract. Trimerizations of isocyanates give isocyanurates (N.N.N-trisubstituted 1,3,5-triazinetriones) in an exothermic, high yield PTC process. Catalysis by various inorganic salts combined with onium salts or crown ethers is effective, Aliquat 336 being the best catalyst.

Cited by 9 publications

References 12 publications

Formation of six-membered palladacycles from phenanthroline Pd(II) bisacetate precursors and phenylisocyanate

Formation of six-membered palladacycles from phenanthroline Pd(II) bisacetate precursors and phenylisocyanate

[P(MeNCH₂CH₂) ₃N], ein effizienter Katalysator für die Umwandlung von Isocyanaten in Isocyanurate

[P(MeNCH₂CH₂)₃N] as a Superior Catalyst for the Conversion of Isocyanates to Isocyanurates

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Onium Salt Catalyzed Preparation of Isocyanurates (Applications of Phase Transfer Catalysis, Part 28 [1])

Abstract: Abstract. Trimerizations of isocyanates give isocyanurates (N.N.N-trisubstituted 1,3,5-triazinetriones) in an exothermic, high yield PTC process. Catalysis by various inorganic salts combined with onium salts or crown ethers is effective, Aliquat 336 being the best catalyst.

Cited by 9 publications

References 12 publications

Formation of six-membered palladacycles from phenanthroline Pd(II) bisacetate precursors and phenylisocyanate

Formation of six-membered palladacycles from phenanthroline Pd(II) bisacetate precursors and phenylisocyanate

[P(MeNCH2CH2) 3N], ein effizienter Katalysator für die Umwandlung von Isocyanaten in Isocyanurate

[P(MeNCH2CH2)3N] as a Superior Catalyst for the Conversion of Isocyanates to Isocyanurates

Contact Info

Product

Resources

About

[P(MeNCH₂CH₂) ₃N], ein effizienter Katalysator für die Umwandlung von Isocyanaten in Isocyanurate

[P(MeNCH₂CH₂)₃N] as a Superior Catalyst for the Conversion of Isocyanates to Isocyanurates