Iodoform, a New Reagent in the Todd-Atherton Reaction

Mielniczak, Grażyna; Bopusiński, Andrzej

doi:10.1081/scc-120026306

Cited by 37 publications

(14 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[63] The reaction is widely applied and sometimes with little modification. [64][65][66][67] In this respect, when the amino acid 45 in H 2 O/CCl 4 was treated with 1c and TEA, N-(diisopropyloxyphosphoryl)amino acid 46 was isolated (Scheme 19). [64] Furthermore, iodine and H 2 O 2 [66] or copper-catalyzed aerobic conditions could be also used.…”

Section: (A) Pudovik Reactionmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

View full text Add to dashboard Cite

In this study, we report recent investigations of the chemical reactivity of alkyl phosphites mainly trialkyl and dialkyl phosphites with molecules containing different nitrogen-containing compounds reported by us and other research groups over the last twenty five years. Earlier leader important reports were also considered. The reviewed investigations in this article are customized, only according to the type of the nitrogenfunctional groups: [amines (primary, secondary, and tertiary amines), imines, amides, thioamides, nitriles, isocyanates, isothiocyanates, oximes, hydrazones, diazo, and azides]and not according to the site of attack or the final products. Furthermore, the present review article focuses on the synthesis of α-amino-, β-amino-and/or enaminophosphonates. These compounds occupy an important role in pharmaceutical chemistry.2 GRAPHICAL ABSTRACT:

show abstract

Section: (A) Pudovik Reactionmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

View full text Add to dashboard Cite

show abstract

“…It plays a double role since it also acts as a halogenating agent that reacts with phosphite to produce chlorophosphate as an intermediate. However, many other solvents, including dichloromethane, chloroform, diethyl ether [ 35 ], THF [ 31 ], acetonitrile [ 34 ], DMF [ 36 ] and toluene [ 37 ] were also used. In that case a stoichiometric amount of the halogenating agent (CCl 4 , CBrCl 3 ) is usually employed.…”

Section: Reviewmentioning

confidence: 99%

“…Accordingly, the chlorophosphate was formed in the presence of triethylamine. Iodoform (CHI 3 ) is another reagent that can be used as a halide source for the AT reaction [ 37 ]. As shown in Scheme 11 , gaseous anhydrous ammonia was passed through a solution of diethyl phosphite and iodoform in toluene to produce the expected phosphoramidate in good yield (83%).…”

Section: Reviewmentioning

confidence: 99%

Atherton–Todd reaction: mechanism, scope and applications

Corre¹,

Berchel²,

Couthon‐Gourvès³

et al. 2014

Beilstein J. Org. Chem.

145

View full text Add to dashboard Cite

SummaryInitially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to different nucleophiles. The mechanism of this reaction led to controversial reports over the past years and is adequately discussed. We also present the scope of the AT reaction. Finally, we investigate the AT reaction by means of exemplary applications, which mainly concern three topics. First, we discuss the activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction. Next, we examine the AT reaction applied to produce fire retardant compounds. In the last section, we investigate the use of the AT reaction for the production of compounds employed for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years.

show abstract

“…[9] PE-I (alkyl iodide) can be iodinating agents of R 2 PH(¼O) to give a deactivator R 2 PI(¼O) via a non-radical process. [10] In the polymerization, both processes (the productions of activator and deactivator) may be involved, and the relative contributions of the two processes would depend on the R group of the phosphorus hydride R 2 PH(¼O). We examined the St polymerizations with (EtO)PhPH(¼O) (with a phenyl group) and (BuO) 2 PH(¼O) (with no phenyl group) as precursors (Figure 2 (half-filled and open circles, respectively) and Table 1 (entries 6 and 7, respectively)).…”

Section: Styrene (St)mentioning

confidence: 99%

Reversible Chain Transfer Catalyzed Polymerizations (RTCPs) of Styrene and Methyl Methacrylate with Phosphorus Catalysts

Goto

Hirai

Tsujii

et al. 2008

Macromolecular Symposia

View full text Add to dashboard Cite

Phosphorus compounds were employed as catalysts in Reversible Chain Transfer Catalyzed Polymerization (RTCP), a novel class of living radical polymerization (LRP) which we had recently developed. Low-polydispersity polystyrene and poly(methyl methacrylate) with predicted molecular weights were obtained with a fairly high conversion in a fairly short time. These catalysts are particularly featured by their high reactivity hence small amounts being required, low toxicity, and low cost. Some phosphorus catalysts used in this work are among the least expensive catalysts/mediators of LRP developed so far.

show abstract

Iodoform, a New Reagent in the Todd-Atherton Reaction

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 37 publications

References 25 publications

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Atherton–Todd reaction: mechanism, scope and applications

Reversible Chain Transfer Catalyzed Polymerizations (RTCPs) of Styrene and Methyl Methacrylate with Phosphorus Catalysts

Contact Info

Product

Resources

About