ChemInform Abstract: TRIALKYL‐ AND TRIARYL(ISOCYANATOMETHYL)CHLOROPHOSPHORANES

Kozhushko, B. N.; Gumenyuk, A. V.; Paliichuk, Yu. A.; Shokol, V. A.

doi:10.1002/chin.197724284

Cited by 2 publications

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“…P + ,N-acetals, obtained by action of alcohols on the products of reactions of chloro(isocyanato)methane with tertiary phosphines. [381] Entry Product R R' Yield, %…”

Section: Entry Iminium Salt Phosphine Conditionsmentioning

confidence: 99%

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Moiseev¹,

James

2022

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…P + ,N-acetals, obtained by action of alcohols on the products of reactions of chloro(isocyanato)methane with tertiary phosphines. [381] Entry Product R R' Yield, %…”

Section: Entry Iminium Salt Phosphine Conditionsmentioning

confidence: 99%

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Moiseev¹,

James

2022

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Reactions were carried out in methanol by bubbling HCl gas through the substrate solution or by treating it with aqueous HBr or HI [ 29 ]. 1-( N -alkoxycarbonyl)methyltriphenylphosphonium chlorides or bromides ( 4a , R 1 = OR, X = Cl or Br) were obtained by Kozhushko et al in the reaction of triphenylphosphine with chloromethylisocyanate or bromomethylisocyanate and further hydrolysis of the isocyanate group ( Scheme 3 , Method C) [ 30 , 31 ]. In analogous reactions, the corresponding triphenylphosphonium iodides ( 4a , R 1 = OR, X = I) were also obtained by adding methyl iodide in the first step of the synthesis [ 32 ].…”

Section: 1-aminoalkyltriarylphosphonium Derivativesmentioning

confidence: 99%

1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of N-Acyliminium-Type Cations, and Maybe Something More: A Review

et al. 2022

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N-acyliminium-type cations are examples of highly reactive intermediates that are willingly used in organic synthesis in intra- or intermolecular α-amidoalkylation reactions. They are usually generated in situ from their corresponding precursors in the presence of acidic catalysts (Brønsted or Lewis acids). In this context, 1-aminoalkyltriarylphosphonium derivatives deserve particular attention. The positively charged phosphonium moiety located in the immediate vicinity of the N-acyl group significantly facilitates Cα-P+ bond breaking, even without the use of catalyst. Moreover, minor structural modifications of 1-aminoalkyltriarylphosphonium derivatives make it possible to modulate their reactivity in a simple way. Therefore, these types of compounds can be considered as smart synthetic equivalents of N-acyliminium-type cations. This review intends to familiarize a wide audience with the unique properties of 1-aminoalkyltriarylphosphonium derivatives and encourage their wider use in organic synthesis. Hence, the most important methods for the preparation of 1-aminoalkyltriarylphosphonium salts, as well as the area of their potential synthetic utilization, are demonstrated. In particular, the structure–reactivity correlations for the phosphonium salts are discussed. It was shown that 1-aminoalkyltriarylphosphonium salts are not only an interesting alternative to other α-amidoalkylating agents but also can be used in such important transformations as the Wittig reaction or heterocyclizations. Finally, the prospects and limitations of their further applications in synthesis and medicinal chemistry were considered.

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ChemInform Abstract: TRIALKYL‐ AND TRIARYL(ISOCYANATOMETHYL)CHLOROPHOSPHORANES

Abstract: Triarylphosphine (I) und Chlormethylisocyanat (II) reagieren zu den monomeren, kristallinen, in Äther unlöslichen Triaryl‐(isocyanatomethyl)‐chlorphosphoranen (III).

Cited by 2 publications

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Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of N-Acyliminium-Type Cations, and Maybe Something More: A Review

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ChemInform Abstract: TRIALKYL‐ AND TRIARYL(ISOCYANATOMETHYL)CHLOROPHOSPHORANES

Abstract: Triarylphosphine (I) und Chlormethylisocyanat (II) reagieren zu den monomeren, kristallinen, in Äther unlöslichen Triaryl‐(isocyanatomethyl)‐chlorphosphoranen (III).

Cited by 2 publications

References 0 publications

Phospha-Mannich reactions of RPH2, R2PH, and R3P

Phospha-Mannich reactions of RPH2, R2PH, and R3P

1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of N-Acyliminium-Type Cations, and Maybe Something More: A Review

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Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P