Über die (thermische) Umlagerung von Thion‐Kohlensäure‐estern in Thiol‐kohlensäure‐ester. (16. Mitteil.) über organische Schwefelverbindungen.)

Schönberg, Alexander; Vargha, L.

doi:10.1002/cber.19300630125

Cited by 59 publications

(14 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Yet, effective synthetic methods for aryl thiols are still much needed due to the scarcity of concise and mild conditions leading to a wide spectrum of aryl thiols. Most of conventional methods including Leuckart thiophenol synthesis,2 Newman–Kwart reaction,3 and Schoenberg reaction4 require multistep syntheses involving diazotization and/or thermal rearrangement at 200–300 °C. Reduction of arylsulfonyl chlorides5 or diaryl polysulfides6 is often employed, but it is also unfavorable due to the laborious preparation of the specific precursors as well as harsh conditions.…”

Section: Methodsmentioning

confidence: 99%

Quantitative Determination of Cellular Farnesyltransferase Activity: Towards Defining the Minimum Substrate Reactivity for Biologically Relevant Protein Farnesylation

2014

View full text Add to dashboard Cite

Prenylation is a post-translational modification wherein an isoprenoid group is attached to a protein substrate by a protein prenyltransferase. Hundreds of peptide sequences are in vitro substrates for protein farnesyltransferase (FTase), but it remains unknown which of these sequences can successfully compete for in vivo prenylation. Translating in vitro studies to predict in vivo protein farnesylation requires determining the minimum reactivity needed for modification by FTase within the cell. Towards this goal, we developed a reporter protein series spanning several orders of magnitude in FTase reactivity as a calibrated sensor for endogenous FTase activity. Our approach provides a minimally invasive method to monitor changes in cellular FTase activity in response to environmental or genetic factors. Determining the reactivity "threshold" for in vivo prenylation will help define the prenylated proteome and identify prenylation-dependent pathways for therapeutic targeting.

show abstract

Section: Methodsmentioning

confidence: 99%

Quantitative Determination of Cellular Farnesyltransferase Activity: Towards Defining the Minimum Substrate Reactivity for Biologically Relevant Protein Farnesylation

2014

View full text Add to dashboard Cite

show abstract

“…Sehr ähnlich zu den obigen Reaktionen, die fünfgliedrige spiro-Ringstrukturen in ihrem Reaktionsweg aufweisen, werden viergliedrige transiente spiro-Ringstrukturen im Reaktionsweg einer Reihe anderer Umlagerungsreaktionen vorgeschlagen, nämlich fürdie Chapman-, Schçnberg- [93] und Newman-Kwart-Umlagerungen. Vond iesen wurde als erste die Schçnberg-Umlagerung von Diarylthionocarbonaten 281 zu Diarylthiolcarbonaten 282 (Schema 39) intensiv untersucht.…”

Section: Newman-kwart-reaktionen Und Verwandte Umlagerungenunclassified

Konzertierte nukleophile aromatische Substitutionen

Rohrbach¹,

Sutherland-Smith²,

Pang

et al. 2019

Angewandte Chemie

View full text Add to dashboard Cite

Jüngste Entwicklungen in der experimentellen und theoretischen Chemie haben zur Identifizierung einer schnell wachsenden Klasse von nukleophilen aromatischen Substitutionsreaktionen geführt, die einem konzertierten Mechanismus (cSNAr) folgen, und nicht dem klassischen, zweistufigen SNAr‐Mechanismus. Während klassische SNAr‐Reaktionen auf die substantielle Aktivierung des aromatischen Ringes durch elektronenziehende Substituenten angewiesen sind, ist eine solche Aktivierung für den konzertierten Reaktionsverlauf nicht zwingend nötig.

show abstract

“…The Newman-Kwart rearrangement (1→2, Scheme 2) was the last in a series of related rearrangements in which aryl groups migrate intramolecularly between nonadjacent atoms, and that were discovered and developed in the early to mid parts of the last century. The Schönberg rearrangement 8 is the most similar and involves the 1,3migration of an aryl group from oxygen to sulfur (3→4) in a diarylthioncarbonate. The Chapman rearrangement 9 involves an analogous migration but to nitrogen (5→6).…”

Section: Background and Historymentioning

confidence: 99%

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

Lloyd‐Jones¹,

Moseley²,

Renny³

2008

Synthesis

View full text Add to dashboard Cite

This literature review focuses on the thermal rearrangement of O-aryl thiocarbamates to yield the corresponding S-aryl thiocarbamates: the Newman-Kwart rearrangement. The purpose of the review is to highlight the utility of the rearrangement which provides a key step in an efficient route to convert phenols into thiophenols. The scope of the Newman-Kwart rearrangement is illustrated by way of numerous examples of its application to the preparation of Ar-S species ranging from large-scale industrial processes through to the synthesis of complex organic molecules such as ligands and supramolecular structures. The review contains 238 references and covers just over 40 years of the literature, from the first reports of the rearrangement by Edwards and Pianka in 1965 up to mid-2007. 1 Introduction 2 The Newman-Kwart Rearrangement (NKR) 2.1 Background and History 2.2 Preparation of O-Aryl Thiocarbamates for NKR and Subsequent Cleavage 2.3 Mechanism of Rearrangement 2.4 Nonclassical Conditions for Rearrangement 2.5 Allylic and Benzylic Rearrangements 2.

show abstract

Über die (thermische) Umlagerung von Thion‐Kohlensäure‐estern in Thiol‐kohlensäure‐ester. (16. Mitteil.) über organische Schwefelverbindungen.)

Cited by 59 publications

References 8 publications

Quantitative Determination of Cellular Farnesyltransferase Activity: Towards Defining the Minimum Substrate Reactivity for Biologically Relevant Protein Farnesylation

Quantitative Determination of Cellular Farnesyltransferase Activity: Towards Defining the Minimum Substrate Reactivity for Biologically Relevant Protein Farnesylation

Konzertierte nukleophile aromatische Substitutionen

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

Contact Info

Product

Resources

About