Vinyl-λ3-iodanes act as efficient sulfur atom acceptors: vinylic SN2-based strategy for conversion of tertiary thioamides to amides

Literature Information

Publication Date 2002-10-24
DOI 10.1039/B209097J
Impact Factor 6.222
Authors

Masahito Ochiai, Shinji Yamamoto


View Original

Abstract

Exposure of tertiary thioamides to (E)-1-hexenyl(phenyl)-λ3-iodane results in vinylic SN2 reaction to give the inverted (Z)-S-vinylthioimidonium salts, which under alkaline hydrolysis (Na2CO3 or K2CO3) selectively afford amides, while (Z)-S-vinyl thioesters are obtained in high yields via the hydrolysis under acidic conditions (HCl).

Related Literature

The photodissociation of NO2 by visible and ultraviolet light

Iain Wilkinson, Ivan Anton Garcia, Benjamin J. Whitaker, Jean-Benoît Hamard, Valérie Blanchet

2010-11-16 Paper

DOI: 10.1039/C0CP01551B

Ultrafast dynamics through conical intersections and intramolecular vibrational energy redistribution in styrene

A. D. G. Nunn, R. S. Minns, R. Spesyvtsev, M. J. Bearpark, M. A. Robb, H. H. Fielding

2010-11-10 Paper

DOI: 10.1039/C0CP01723J

Thermal and photochemical oxidation of self-assembled monolayers on alumina particles exposed to nitrogen dioxide

Jonathan D. Raff, János Szanyi, Barbara J. Finlayson-Pitts

2010-11-01 Paper

DOI: 10.1039/C0CP01041C

Fast optical vapour sensing by Bloch surface waves on porous siliconmembranes

Francesco Michelotti, Beniamino Sciacca, Lorenzo Dominici, Marzia Quaglio, Emiliano Descrovi, Fabrizio Giorgis, Francesco Geobaldo

2009-11-16 Paper

DOI: 10.1039/B914280K

Interaction of water, hydrogen and their mixtures with SnO2 based materials: the role of surface hydroxyl groups in detection mechanisms

Roman G. Pavelko, Helen Daly, Christopher Hardacre, Alexey A. Vasiliev, Eduard Llobet

2010-01-27 Paper

DOI: 10.1039/B921665K

The zone-refine driven growth of jellyfish-like core–shell nanowires

Jyun-Lin Wu, Hsin-Fu Kuo, Ping-Tzu Chen, Hung-Jen Chen, Su-Jien Lin, Wen-Kuang Hsu

2010-10-25 Paper

DOI: 10.1039/C0CP00890G

Selective internuclear coupling estimation in the solid-state NMR of multiple-spin systems

Andrea C. Sauerwein, Maria Concistrè, Malcolm H. Levitt

2010-10-21 Communication

DOI: 10.1039/C0CP01262A

EXAFS and XRD characterization of palladium sorbents for high temperature mercury capture from fuel gas

Stephen Poulston, Timothy I. Hyde, Hugh Hamilton, Olivier Mathon, Carmelo Prestipino, Andrew W. J. Smith

2009-11-13 Paper

DOI: 10.1039/B911941H

Mercury dications: linear form is more stable than aromatic ring‡

Minh Tho Nguyen, Tamás Veszprémi

2009-11-19 Communication

DOI: 10.1039/B916847H

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Chemical Communications

Chemical Communications
CiteScore: 8.6
Self-citation Rate: 4.7%
Articles per Year: 2458

ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.