Nucleophilic identity substitution reactions. The reaction between hydrogen fluoride and protonated alkyl fluorides

2006 ◽  
Vol 4 (1) ◽  
pp. 135-141 ◽  
Author(s):  
Jon K. Laerdahl ◽  
Pervin U. Civcir ◽  
Lihn Bache-Andreassen ◽  
Einar Uggerud
Keyword(s):  
Hydrogen Fluoride ◽  
Substitution Reactions ◽  
Alkyl Fluorides

Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding

2013 ◽  
Vol 15 (9) ◽  
pp. 2210-2213 ◽  
Author(s):  
Pier Alexandre Champagne ◽  
Julien Pomarole ◽  
Marie-Ève Thérien ◽  
Yasmine Benhassine ◽  
Samuel Beaulieu ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Alkyl Fluorides

ChemInform Abstract: Base-Promoted Elimination of Hydrogen Fluoride from Alkyl Fluorides: Reactivity and Stereochemistry.

ChemInform ◽  
1988 ◽  
Vol 19 (40) ◽  
Author(s):  
S. MATSUBARA ◽  
H. MATSUDA ◽  
T. HAMATANI ◽  
M. SCHLOSSER
Keyword(s):  
Hydrogen Fluoride ◽  
Alkyl Fluorides

Base-promoted elimination of hydrogen fluoride from alkyl fluorides : Reactivity and stereochemistry

Tetrahedron ◽  
1988 ◽  
Vol 44 (10) ◽  
pp. 2855-2863 ◽  
Author(s):  
Seijiro Matsubara ◽  
Hiroyuki Matsuda ◽  
Takeshi Hamatani ◽  
Manfred Schlosser
Keyword(s):  
Hydrogen Fluoride ◽  
Alkyl Fluorides

Spatiotemporal Control of Amide Radicals During Photocatalysis

2020 ◽  
Author(s):  
Shogo Mori ◽  
Takahiro Aoki ◽  
Kaliyamoorthy Selvam ◽  
Shunichi Fukuzumi ◽  
Jieun Jung ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Nickel Complex ◽  
Nickel Complexes ◽  
Semiconductor Material ◽  
Radical Reactions ◽  
Substitution Reactions ◽  
Carbon Neutrality ◽  
Spatiotemporal Control ◽  
Scalable Production ◽  
Salt Waste

Despite the continuing popularity of radical reactions in organic synthesis, much remains to be explored in this area. Herein, we describe how spatiotemporal control can be exerted over the formation and reactivity of divergent exchangeable formamide radicals using nickel complexes with a semiconductor material (TiO<sub>2</sub>) under irradiation from near-UV–Vis light. Depending on the bipyridine ligand used and the quantity of the nickel complex that is hybridized on or nonhydridized over the TiO<sub>2</sub> surface, these radicals selectively undergo substitution reactions at the carbon center of carbon–bromine bonds that proceed via three different pathways. As the scalable production of formamides from CO<sub>2</sub> does not produce salt waste, these methods could add a new dimension to the search for carbon neutrality through the indirect incorporation of CO<sub>2</sub> into organic frameworks.

Tele-Substitution Reactions in the Synthesis of a Promising Class of Antimalarials

2020 ◽  
Author(s):  
Marat Korsik ◽  
Edwin Tse ◽  
David Smith ◽  
William Lewis ◽  
Peter J. Rutledge ◽  
...  
Keyword(s):  
Heterocyclic Ring ◽  
Ring System ◽  
Substitution Reactions ◽  
Laboratory Notebook ◽  
Polar Solvents ◽  
X Ray ◽  
X Ray Crystallography ◽  
The Core ◽  
Nmr Data

<p></p><p>We have discovered and studied a <i>tele</i>substitution reaction in a biologically important heterocyclic ring system. Conditions that favour the <i>tele</i>-substitution pathway were identified: the use of increased equivalents of the nucleophile or decreased equivalents of base, or the use of softer nucleophiles, less polar solvents and larger halogens on the electrophile. Using results from X-ray crystallography and isotope labelling experiments a mechanism for this unusual transformation is proposed. We focused on this triazolopyrazine as it is the core structure of the <i>in vivo </i>active anti-plasmodium compounds of Series 4 of the Open Source Malaria consortium.</p> <p> </p> <p>Archive of the electronic laboratory notebook with the description of all conducted experiments and raw NMR data could be accessed via following link <a href="https://ses.library.usyd.edu.au/handle/2123/21890">https://ses.library.usyd.edu.au/handle/2123/21890</a> . For navigation between entries of laboratory notebook please use file "Strings for compounds in the article.pdf" that works as a reference between article codes and notebook codes, also this file contain SMILES for these compounds. </p><br><p></p>

Sign in / Sign up

Export Citation Format

Share Document