𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Hetarenium salts from pentafluoropyridine. Syntheses, spectroscopic properties, and applications

✍ Scribed by Andreas Schmidt; Thorsten Mordhorst; Jan Christoph Namyslo; Werner Telle

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
529 KB
Volume
44
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image

Reaction of pentafluoropyridine with nucleophilic heteroaromatics such as 4‐(dimethylamino)pyridine, 4‐(pyrrolidin‐1‐yl)pyridine, 4‐(morpholin‐4‐yl)pyridine, 4‐aminopyridine, and 3,4‐diaminopyridine resulted in the formation of 4‐hetarenium substituted tetrafluoropyridines. The 4‐(dimethylamino)‐pyridinium derivative underwent substitution reactions with isopropanolate, isopropanethiolate, and benzylthiolate to F^2^,F^3^,O^4^,F^5^,F^6^‐ and O^2^,F^3^,O^4^,F^5^,F^6^‐pentasubstituted pyridines as well as their sulfur analogs. N‐Propylamine, isopropylamine, and piperidine formed 4‐amino‐N^2^,F^3^,F^5^,F^6^‐pentasubstituted pyridines in the presence of sodium amide as base, whereas morpholine gave the 4‐amino‐2,6‐bis‐morpholino‐substituted 3,5‐difluoropyridine. ^19^F, ^15^N, ^13^C, and ^1^H nmr spectrocopy was performed to elucidate the structures of the substitution products.

📜 SIMILAR VOLUMES

Sterospecific Syntheses and Spectroscopi
Sterospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae. Part IV.
✍ Wilhelm Boland; Nora Schroer; Christiane Sieler; Martin Feigel 📂 Article 📅 1987 🏛 John Wiley and Sons 🌐 German ⚖ 908 KB

Giffordene ( = (22,42,6E,82)-2,4,6,8-~ndecatetraene; 9f) and five stereoisomers are new C , ,HI, hydrocarbons from the marine brown alga G$fordia mitchellae. Their synthesis is based on non-stereoselective Wittig reactions of (E)-2-alkenals with appropriate acetylenic phosphoranes and subsequent chr

Syntheses, Structures, and Properties of
Syntheses, Structures, and Properties of Two-Dimensional Honeycomb Networks from the Assembly of the Tripodal Ligand 2,4,6-Tris[4-(imidazol-1-ylmethyl)phenyl]-1,3,5-triazine with Metal Salts
✍ Shuang-Yi Wan; Yi-Zhi Li; Taka-aki Okamura; Jian Fan; Wei-Yin Sun; Norikazu Ueya 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 218 KB 👁 1 views

## Abstract Two novel coordination networks, [Zn~2~(timpt)~2~(μ‐OH)](NO~3~)~3~ (1) and [Ni~2~(timpt)~2~(H~2~O)~2~(SO~4~)~2~]·0.5H~2~O (2) were obtained by assembly of 2,4,6‐tris[4‐(imidazol‐1‐ylmethyl)phenyl]‐1,3,5‐triazine (timpt) with the corresponding metal salts. The X‐ray single‐crystal diffra

ChemInform Abstract: Pyridinium N-Phenox
ChemInform Abstract: Pyridinium N-Phenoxide Betaines and Their Application to the Determination of Solvent Polarities. Part 25. Syntheses and UV/Vis-Spectroscopic Properties of Hydrophilic 2-, 3-, and 4-Pyridyl-Substituted Solvatochromic and Halochromic Pyridinium N-Phenolate Betaine Dyes as New Empirical Solvent Polarity Indicators.
✍ Christian Reichardt; Daqing Che; Guido Heckenkemper; Gerhard Schaefer 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 1 views