Thiocarbonyls. III. The Willgerodt Reaction with Thioacetophenone<sup>1</sup>

Campaigne, E.; Rutan, Phyllis V.

doi:10.1021/ja01197a501

Cited by 12 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Two essential reagents, namely phosphorus pentasulfide (P 4 S 10 ) and Lawesson's reagent (LR) (Figure 1), are the most widely used agents for such a transformation. However, as the most commonly used reagent since the beginning of the 20th century, LR has gained the upper hand with essential applications in synthetic organic chemistry [1][2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

View full text Add to dashboard Cite

Lawesson’s reagent (LR) is a well-known classic example of a compound with unique construction and unusual chemical behavior, with a wide range of applications in synthetic organic chemistry. Its main functions were rounded for the thionation of various carbonyl groups in the early days, with exemplary results. However, the role of Lawesson’s reagent in synthesis has changed drastically, and now its use can help the chemistry community to understand innovative ideas. These include constructing biologically valuable heterocycles, coupling reactions, and the thionation of natural compounds. The ease of availability and the convenient usage of LR as a thionating agent made us compile a review on the new diverse applications on some common functional groups, such as ketones, esters, amides, alcohols, and carboxylic acids, with biological applications. Since the applications of LR are now diverse, we have also included some new classes of heterocycles such as thiazepines, phosphine sulfides, thiophenes, and organothiophosphorus compounds. Thionation of some biologically essential steroids and terpenoids has also been compiled. This review discusses the recent insights into and synthetic applications of this famous reagent from 2009 to January 2021.

show abstract

Section: Introductionmentioning

confidence: 99%

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

View full text Add to dashboard Cite

show abstract

C ₃ S ₃ Ring Systems

1966

Chemistry of Heterocyclic Compounds: A Series of Monographs

View full text Add to dashboard Cite

Willgerodt‐Kindler Reaction

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

The preparation of thionamide from the reaction of an organic molecule (from acetophenone and anhydrous primary or secondary amines) with sulfur and amine is generally called the Willgerodt–Kindler reaction. Occasionally, this reaction is also termed as the Willgerodt–Kindler redox amidation. The resulting thionamides are further converted into carbonamides by hot aqueous ammonia under the Willgerodt condition. The high boiling point of morpholine, an intrinsic feature, allows the Willgerodt–Kindler reaction to take place in an open vessel instead of an autoclave or a sealed tube. For comparison, under the condition of Willgerodt reaction, it has been found that the presence of pyridine is beneficial to the reaction by lowering the reaction temperature from 210°C to 165°C and raising the yield of phenylacetamide from 49% to 64%. It has been reported that the ketones with a straight chain usually give much better yields of amides than the branched ketones with the same number of carbon atoms at the main chains under comparable reaction conditions. Furthermore, the yields of amide from ketones decrease inversely with the increase of chain length of the alkyl groups. Moreover, the amount of sulfur has also been found to be critical. This reaction has very broad application in the preparation of thionamides and carboxylic acids.

show abstract

Thiocarbonyls. III. The Willgerodt Reaction with Thioacetophenone¹

Cited by 12 publications

References 0 publications

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

C ₃ S ₃ Ring Systems

Willgerodt‐Kindler Reaction

Contact Info

Product

Resources

About

Thiocarbonyls. III. The Willgerodt Reaction with Thioacetophenone1

Cited by 12 publications

References 0 publications

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

C 3 S 3 Ring Systems

Willgerodt‐Kindler Reaction

Contact Info

Product

Resources

About

Thiocarbonyls. III. The Willgerodt Reaction with Thioacetophenone¹

C ₃ S ₃ Ring Systems