Retraction: One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

• Mohammad Abbasi and
• Reza Khalifeh

Beilstein J. Org. Chem. 2023, 19, 1170–1170, doi:10.3762/bjoc.19.85

• Mohammad Abbasi Reza Khalifeh Chemistry Department, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran Department of Chemistry, Shiraz University of Technology, Shiraz, Iran 10.3762/bjoc.19.85 Keywords: benzoic anhydride; Michael addition; nucleophilic displacement; thioester

Friedel–Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs)

• Swantje Lerch,
• Stefan Fritsch and
• Thomas Strassner

Beilstein J. Org. Chem. 2023, 19, 212–216, doi:10.3762/bjoc.19.20

• via GC–MS). The products were isolated via flash column chromatography to determine the yield. Anthracene was selectively acylated at the 9-position (14) using acetic anhydride. The use of other anhydrides was also tested: propionic anhydride and benzoic anhydride lead to yields between 41% and 92

A metal-free approach for the synthesis of amides/esters with pyridinium salts of phenacyl bromides via oxidative C–C bond cleavage

• Kesari Lakshmi Manasa,
• Yellaiah Tangella,
• Namballa Hari Krishna and
• Mallika Alvala

Beilstein J. Org. Chem. 2019, 15, 1864–1871, doi:10.3762/bjoc.15.182

• work-up procedures and the requirement of stoichiometric amounts of coupling reagents. On the other hand, benzoylation reactions are usually performed with benzoyl chloride or benzoic anhydride which results in the formation of a substantial amount of undesired chemical waste. Moreover, these benzoic

Mechanochemical Friedel–Crafts acylations

• Mateja Đud,
• Anamarija Briš,
• Iva Jušinski,
• Davor Gracin and
• Davor Margetić

Beilstein J. Org. Chem. 2019, 15, 1313–1320, doi:10.3762/bjoc.15.130

• were less reactive in comparison to phthalic anhydride. Benzoic anhydride was used as a substitute for benzoyl chloride and the reaction proceeded in better yield. The observed disparity in reactivity might be associated with the difference in the physical state of the reagents. Furthermore, succinic

Mechanochemistry of nucleosides, nucleotides and related materials

• Olga Eguaogie,
• Joseph S. Vyle,
• Patrick F. Conlon,
• Manuela A. Gîlea and
• Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

• cytosine was also effected following addition of benzoic anhydride and catalytic DMAP to the crude reaction mixture and extending the milling time. Quantitative silylation of 5′-O-dimethoxytritylthymidine under these conditions was also reported. Prompted by the insolubility of adenosine 5′-carboxylic acid

One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

• Mohammad Abbasi and
• Reza Khalifeh

Beilstein J. Org. Chem. 2015, 11, 1265–1273, doi:10.3762/bjoc.11.141

• reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides. Keywords: benzoic anhydride; Michael addition; nucleophilic displacement; thioester; thiourea; Introduction Thioesters have

• reaction between thiourea and carboxylic anhydrides was investigated. As a model reaction, a mixture of well-powdered benzoic anhydride (1 mmol) and thiourea (1.1 mmol) in Et3N (0.5 mL) was stirred at 40 °C. The starting benzoic anhydride was gradually consumed within 0.5 h and a two-phase system

• % yield. We then focused our attention on developing a practical method to prepare thia-Michael adducts of thioacids. In this regard, a mixture of benzoic anhydride and thiourea in Et3N was stirred at 40 °C for 0.5 h. Then, water and n-butyl acrylate were added to the mixture and stirring was continued

Visible light photoredox-catalyzed deoxygenation of alcohols

• Daniel Rackl,
• Viktor Kais,
• Peter Kreitmeier and
• Oliver Reiser

Beilstein J. Org. Chem. 2014, 10, 2157–2165, doi:10.3762/bjoc.10.223

• microreactor (see Supporting Information File 1). Conclusion In summary a protocol for the deoxygenation of benzylic alcohols, α-hydroxycarbonyl and α-cyanohydrin compounds under visible light photocatalysis was developed using 3,5-bis(trifluoromethyl)benzoic anhydride for alcohol activation. Since 3,5-bis

Chiral phosphines in nucleophilic organocatalysis

• Yumei Xiao,
• Zhanhu Sun,
• Hongchao Guo and
• Ohyun Kwon

Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate

• James A. B. Laurenson,
• John A. Parkinson,
• Jonathan M. Percy,
• Giuseppe Rinaudo and
• Ricard Roig

Beilstein J. Org. Chem. 2013, 9, 2660–2668, doi:10.3762/bjoc.9.301

• % respectively. The ee's were measured after conversion of the diols to the dibenzoates 29 upon stirring overnight with benzoic anhydride, DMAP and polyvinylpyridine (PVP) at room temperature. The removal of the base by filtration was facile (Scheme 6). Genuine racemate 28c was synthesised via the Upjohn

• the crude reaction mixture (Scheme 7) by treatment of the crude monobenzoate 33b with benzoic anhydride in the presence of DMAP and PVP. The syn- and anti-dibenzoates have distinct signals in the 19F NMR spectra (δF −230.3 and −231.0 ppm respectively), allowing a very high level of confidence that the