scholarly journals NUCHLEOPHILIC SUBSTITUTION REACTION OF CYANIDE AND METHOXYDE IONS TO QUATERNARY MANNICH BASE FROM VANILLIN

2010 ◽  
Vol 7 (1) ◽  
pp. 58-60
Author(s):  
Bambang Purwono ◽  
Estiana E.P Daruningsih
Keyword(s):  
Nucleophilic Substitution ◽  
Mannich Reaction ◽  
Quaternary Ammonium ◽  
Substitution Reaction ◽  
Mannich Base ◽  
Nucleophilic Substitution Reaction ◽  
Nucleophilic Reaction ◽  
Halide Salt ◽  
Dimethyl Amine ◽  
Halide Salts

The nucleophilic substitution reaction to quaternary Mannich base from vanillin has been investigated. Mannich reaction to vanillin was carried out by refluxing mixture of vanillin, formaldehyde and dimethyl amine. Quaternary ammonium halide salt was obtained from reaction of Mannich vanillin base with methyl iodide in THF solvents and yielded  93.28%. Nucleophilic substituion to the halide salts with cyanide nucleophile produced 4-hidroxy-3-methoxy-5-(cyano)methylbenzaldehyde in 54.39% yield, with methoxyde ion obtained  4-hidroxy- 3-methoxy-5-(methoxy)-methyl-benzaldehide in 67.80% yield. The nucleophilic substitution reaction showed that substituen of trimethylamino quaternary Mannich base can act as a good leaving on nucleophilic reaction substitutions.   Keywords: Mannich Reaction, Vanillin, nucleophilic substitution.

scholarly journals NUCLEOPHILIC SUBSTITUTION REACTION OF CYANIDE AND METHOXYDE IONS TO QUATERNARY MANNICH BASE FROM VANILLIN

2010 ◽  
Vol 5 (3) ◽  
pp. 203-206
Author(s):  
Bambang Purwono ◽  
Estiana R. P. Daruningsih
Keyword(s):  
Nucleophilic Substitution ◽  
Mannich Reaction ◽  
Substitution Reaction ◽  
Mannich Base ◽  
Nucleophilic Substitution Reaction ◽  
Substitution Reactions ◽  
Halide Salt ◽  
Leaving Group ◽  
Dimethyl Amine ◽  
Halide Salts

The nucleophilic substitution reaction to quaternary Mannich base from vanillin has been investigated. Mannich reaction to vanillin was carried out by refluxing mixture of vanillin, formaldehyde and dimethyl amine. Quaternary ammonium halide salt was obtained from reaction of Mannich vanillin base with methyl iodide in THF solvents and yielded 93.28 %. Nucleophilic substituion to the halide salts with cyanide nucleophile produced 4-hidroxy-3-methoxy-5-(cyano)methylbenzaldehyde in 54.39% yield. Reaction with methoxyde ion yielded 4-hydroxy- 3-methoxy-5-(methoxy) -methylbenzaldehyde in 67.80% yield. The nucleophilic substitution reaction showed that trimethylamino substituent of quaternary Mannich base can act as a good leaving group on nucleophilic substitution reactions. Keywords: Mannich reaction, vanillin, nucleophilic substitution

Radical mechanism of a nucleophilic reaction depending on a two-dimensional structure

2018 ◽  
Vol 20 (1) ◽  
pp. 489-497 ◽  
Author(s):  
Wenchuan Lai ◽  
Yuehui Yuan ◽  
Xu Wang ◽  
Yang Liu ◽  
Yulong Li ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Dimensional Structure ◽  
Radical Mechanism ◽  
Two Dimensional ◽  
Nucleophilic Reaction ◽  
Two Dimensional Materials ◽  
Fluorinated Graphene

This study reveals the radical mechanism of the nucleophilic substitution reaction of fluorinated graphene depending on its two-dimensional structure, which can be used to represent the chemistry characteristics of two-dimensional materials while enriching the research on nucleophilic substitution in the field of organic chemistry.

scholarly journals Influence of the milling parameters on the nucleophilic substitution reaction of activated β-cyclodextrins

2017 ◽  
Vol 13 ◽  
pp. 1893-1899 ◽  
Author(s):  
László Jicsinszky ◽  
Kata Tuza ◽  
Giancarlo Cravotto ◽  
Andrea Porcheddu ◽  
Francesco Delogu ◽  
...  
Keyword(s):  
Stainless Steel ◽  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Planetary Mill ◽  
Nucleophilic Substitution Reaction ◽  
Nucleophilic Reaction ◽  
Milling Parameters ◽  
Milling Tools

The present work focuses on the mechanochemical preparation of industrially important β-cyclodextrin (CD) derivatives. Activated CDs have been reacted with nitrogen and sulfur nucleophiles using a planetary mill equipped with stainless steel, zirconia and glass milling tools of different sizes. It is shown that the milling frequency and the number as well as the size of the milling balls have an effect on the nucleophilic reaction.

scholarly journals Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3394
Author(s):  
Surya B. Adhikari ◽  
Anji Chen ◽  
Guijun Wang
Keyword(s):  
Nucleophilic Substitution ◽  
Supramolecular Chemistry ◽  
Copper Sulfate ◽  
Substitution Reaction ◽  
Biological Properties ◽  
Anion Binding ◽  
Nucleophilic Substitution Reaction ◽  
Binding Properties ◽  
Intramolecular Nucleophilic Substitution ◽  
Leaving Groups

Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

Lewis-Acid-Catalyzed Direct Nucleophilic Substitution Reaction of Alcohols for the Functionalization of Aromatic Amines

2019 ◽  
Vol 4 (4) ◽  
pp. 1371-1374 ◽  
Author(s):  
Onkar S. Nayal ◽  
Maheshwar S. Thakur ◽  
Rohit Rana ◽  
Rahul Upadhyay ◽  
Sushil K. Maurya
Keyword(s):  
Nucleophilic Substitution ◽  
Lewis Acid ◽  
Aromatic Amines ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Acid Catalyzed

Synthesis of Steroid–Porphyrin Conjugates from Oestradiol, Oestrone, and Lithocholic Acid

2014 ◽  
Vol 67 (11) ◽  
pp. 1632 ◽  
Author(s):  
Fargol Taba ◽  
Tze Han Sum ◽  
Paul J. Sintic ◽  
Ann H. Lundmark ◽  
Maxwell J. Crossley
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Lithocholic Acid ◽  
The Other ◽  
Nucleophilic Substitution Reaction ◽  
Porphyrin Synthesis ◽  
Synthesis Reactions ◽  
Steroid Conjugates ◽  
The Way

The synthesis of porphyrin–steroid conjugates is examined using the natural steroids oestradiol, oestrone, and lithocholic acid as precursors. Two strategies differing in the timing of formation of the steroid–porphyrin linkage leading to four different construction motifs are explored. Two approaches are based on a strategy of introduction of steroidal components in the porphyrin-forming reaction involving condensation of steroidal-alkylaldehydes and pyrrole to give 5,10,15,20-tetrakis(steroidal-alkyl)porphyrins and differ in the way in which the required aldehyde is introduced to the steroidal component. In the other strategy, a steroidal component is introduced by post-porphyrin synthesis reactions and here also two approaches were explored, one involving nucleophilic substitution and the other esterification. Of the four approaches investigated, the most efficient and most versatile one attaches the steroidal components late in the sequence to a 5,10,15,20-tetra(ω-haloalkyl)porphyrin by a nucleophilic substitution reaction. In this way, a 5,10,15,20-tetrakis[oestrone-linked-heptyl)porphyrin was obtained in 47 % yield.

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