Solvent and counterion control of stereochemistry in a formal nucleophilic displacement reaction. Mechanisms of reaction of trimethyltin alkalis with alkyl halides

1972 ◽  
Vol 94 (20) ◽  
pp. 7206-7208 ◽  
Author(s):  
H. G. Kuivila ◽  
J. L. Considine ◽  
J. D. Kennedy
Keyword(s):  
Reaction Mechanisms ◽  
Alkyl Halides ◽  
Displacement Reaction ◽  
Nucleophilic Displacement

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

2015 ◽  
Vol 11 ◽  
pp. 1265-1273 ◽  
Author(s):  
Mohammad Abbasi ◽  
Reza Khalifeh
Keyword(s):  
Conjugate Addition ◽  
Alkyl Halides ◽  
Displacement Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Organic Halides ◽  
Nucleophilic Displacement ◽  
In Situ Generation

An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.

1-ChIoromethyl-3,5-dimethylpyrazole hydrochloride. A useful synthetic intermediate

1989 ◽  
Vol 67 (7) ◽  
pp. 1144-1147 ◽  
Author(s):  
Alan R. Katritzky ◽  
Jamshed N. Lam
Keyword(s):  
Carbonyl Compounds ◽  
Alkyl Halides ◽  
Nucleophilic Displacement ◽  
Novel Method ◽  
Synthetic Intermediate ◽  
Substituted Pyrazoles

1-Chloromethyl-3,5-dimethylpyrazole hydrochloride readily undergoes nucleophilic displacement with O-, N-, or S-nu-cleophiles. 1-Phenylthiomethyl-3,5-dimethylpyrazole can be lithiated at the CH2 group and reacted with alkyl halides and carbonyl compounds. Desulfurization of the products affords a novel method of preparing N-substituted pyrazoles. Keywords: pyrazole, lithiation, chloromethylazoles, desulfurization.

Reactions in microemulsion media. Nucleophilic displacement reaction of benzyl chloride with bromide ion

1982 ◽  
Vol 23 (45) ◽  
pp. 4651-4654 ◽  
Author(s):  
Craig A. Martin ◽  
Patrick M. MgCrann ◽  
George H. Angelos ◽  
David A. Jaeger
Keyword(s):  
Benzyl Chloride ◽  
Displacement Reaction ◽  
Nucleophilic Displacement ◽  
Bromide Ion

Recent advances in the synthesis of 5'-deoxynucleoside phosphonate analogs

2021 ◽  
Vol 28 ◽  
Author(s):  
Guang Huan Shen ◽  
Joon Hee Hong
Keyword(s):  
Biological Activity ◽  
Radical Reaction ◽  
Cross Coupling ◽  
Mitsunobu Reaction ◽  
Addition Reactions ◽  
Arbuzov Reaction ◽  
Displacement Reaction ◽  
Cross Metathesis ◽  
Nucleophilic Displacement ◽  
Vinyl Phosphonates

: The present review focuses on the synthesis of cyclic 5-deoxynucleoside phosphonate analogs. The formation of various phosphonate alkyl moieties is accomplished through (i) Wittig (or HWE) type condensation to the nucleoside aldehyde moiety; (ii) nucleophilic displacement reaction using phosphonate anion or Lewis acid; (iii) Arbuzov reaction; (iv) olefin cross-metathesis between vinyl phosphonates and vinylated nucleosides; and (v) radical reaction and Pd catalyzed alkyne. For the coupling of nucleobases with cyclic moieties, the Mitsunobu reaction, and Sonogashira-type cross-coupling are usually applied. For the coupling of furanose moieties with nucleobases, Vorbrüggen-type condensation is generally applied. Addition reactions mediated by selenium ions are mainly applied for the coupling of carbocyclic moieties. Their biological activity results are summarized.

Intramolecular van der Waals-London Cohesions and Chemical Reactivity: The Transition State in the Bimolecular Nucleophilic Displacement Reaction of Halide Ion with Alkyl Halide

1960 ◽  
Vol 13 (2) ◽  
pp. 218 ◽  
Author(s):  
E Spinner
Keyword(s):  
Transition State ◽  
Halogen Atom ◽  
Significant Contribution ◽  
Chemical Reactivity ◽  
Alkyl Halide ◽  
Van Der Waals ◽  
Transition States ◽  
Displacement Reaction ◽  
Kcal Mole ◽  
Nucleophilic Displacement

The intramolecular London-van der Waals cohesions in the transition states Hal�-. . . CH3 . . . Hal�- in which both halogen atoms are identical should be greater than the following : Hal=F, 0.09 ; Hal=Cl, 0.64 ; Hal=Br, 0.94 ; Hal=I, 1.15 kcal/mole. It is concluded that these cohesions make a significant contribution to the observed increase in the velocity of the above displacement reaction as the polarizability of either entering or leaving halogen atom increases.

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