𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Reactions of polycyclic thioketones with a phosphonylated carbanion

✍ Scribed by Grzegorz Mloston; Emilia Obijalska; Katarzyna Urbaniak; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
213 KB
Volume
19
Category
Article
ISSN
1042-7163

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Polycyclic, nonenolizable cycloaliphatic thioketones 1a and 1b react smoothly with the lithium salt of diethyl methylphosphonate 7 in THF solution at −40°C to afford products of the carbophilic attack exclusively. Quenching of the obtained lithium thiolates with alkyl iodides yields sulfanes of type 9 or 11, respectively, in good yields. 1‐Fluoro‐2,4‐dinitrobenzene was shown to act as an arylating agent. In the case of the “cage” thioketone 1b, the carbanion of salt 7 approaches the CS bond from the exo‐side exclusively. In contrast to the parent carbonyl compounds, thioketones 1 show no tendency to undergo the conversion analogous to the Horner–Wadsworth–Emmons reaction, which would result in the formation of an olefinic product. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:182–187, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20390

📜 SIMILAR VOLUMES

Formation of Phosphonylated Thiiranes in
Formation of Phosphonylated Thiiranes in the Reaction of a Diazomethanephosphonate and Cycloaliphatic Thioketones.
✍ Grzegorz Mloston; Katarzyna Urbaniak; Stanislaw Lesniak; Piotr Wasiak; Heinz Hei 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 25 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Reactions of Thioketones with Dichloroca
Reactions of Thioketones with Dichlorocarbene
✍ Grzegorz Mlostoń; Jaroslaw Romański; Anna Swia¸tek; Heinz Heimgartner 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 German ⚖ 159 KB 👁 1 views

## Âczyk on the occasion of his 60th birthday The reactions of sterically crowded cycloalkanethiones of type 2 with CHCl 3 /NaOH under phase-transfer catalysis (PTC) with benzyl(triethyl)ammonium chloride (TEBA) as catalyst afforded the corresponding gem.dichlorothiiranes of type 3 in good yields

Reactions of Thioketones with a Fluorina
Reactions of Thioketones with a Fluorinated Thione S-Imide
✍ Grzegorz Mloston; Malgorzata Celeda; Herbert W. Roesky; Emilio Parisini; Jens-Th 📂 Article 📅 1998 🏛 John Wiley and Sons 🌐 English ⚖ 546 KB

Thione S-imides / Thiaziridines / Thione S-sulfides (thiosulfines) / Sulfur heterocycles / Reaction mechanism N-(1-Adamantyl)hexafluorothioacetone S-imide (1) reacts product. The structure of 9 has been determined by X-ray diffraction analysis. The connectivity of the heterocyclic ring readily with