scholarly journals The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 6000
Author(s):  
Yulia V. Khoroshunova ◽  
Denis A. Morozov ◽  
Andrey I. Taratayko ◽  
Sergey A. Dobrynin ◽  
Ilia V. Eltsov ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Hydroxyl Group ◽  
Methanesulfonyl Chloride ◽  
Functional Derivatives ◽  
Hofmann Elimination

Activation of a hydroxyl group towards nucleophilic substitution via reaction with methanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl- 1-azaspiro[4.4]nonanes 1a–d (Х = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahydro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocyclopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.

ChemInform Abstract: NUCLEOPHILIC SUBSTITUTION OF THE HYDROXYL GROUP OF 2-ALKYL(ARYL)THIOETHANOLS

1983 ◽  
Vol 14 (10) ◽  
Author(s):  
A. V. FOKIN ◽  
A. F. KOLOMIETS ◽  
L. S. RUDNITSKAYA ◽  
M. G. IZNOSKOVA ◽  
L. S. PAIMULKINA
Keyword(s):  
Nucleophilic Substitution ◽  
Hydroxyl Group ◽  
Alkyl Aryl

ChemInform Abstract: Broensted Acid-Catalyzed Intramolecular Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer.

ChemInform ◽  
2015 ◽  
Vol 46 (38) ◽  
pp. no-no
Author(s):  
Anon Bunrit ◽  
Christian Dahlstrand ◽  
Sandra K. Olsson ◽  
Pemikar Srifa ◽  
Genping Huang ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Hydroxyl Group ◽  
Chirality Transfer ◽  
Intramolecular Nucleophilic Substitution ◽  
Acid Catalyzed

scholarly journals SYNTHESIS 7-O-CARBOXYMETHYL-3’,4’-DIMETHOXYISOFLAVONE

2012 ◽  
Vol 12 (3) ◽  
pp. 242-246
Author(s):  
Andi Hairil Alimuddin ◽  
Sabirin Matsjeh ◽  
Chairil Anwar ◽  
Mustofa Mustofa
Keyword(s):  
Melting Point ◽  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Ester Group ◽  
Nucleophilic Substitution Reaction ◽  
Hydroxyl Group ◽  
Hydrolysis Of

Synthesis of 7-O-carboxymethyl-3',4'-dimethoxyisoflavone from 7-hydroxy-3',4'-dimethoxyisoflavone derived from eugenol had been done. 7-hydroxy-3',4'-dimethoxyisoflavone was first converted into 7-O-ethoxycarbonylmethyl-3',4'-dimethoxyisoflavone via substitution of hydroxyl group at 7-O position by ethyl-2 chloro acetate through bimolecular nucleophilic substitution reaction (SN2). Hydrolysis of ester group of 7-O-ethoxycarbonylmethyl-3',4'-dimethoxyisoflavone using KOH produce 7-O-carboxymethyl-3',4'-dimethoxyisoflavone in 93.4% yield as a white solid with melting point of 155-159 °C.

Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer

Synlett ◽  
2015 ◽  
Vol 27 (02) ◽  
pp. 173-176
Author(s):  
Joseph Samec ◽  
Anon Bunrit ◽  
Christian Dahlstrand ◽  
Pemikar Srifa ◽  
Sandra Olsson ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Hydroxyl Group ◽  
Chirality Transfer

scholarly journals SYNTHESIS OF 2- (2I – ACYLOXY-ETHOXY) ETHYL CHLORIDE AND THEIR INTERACTION WITH AMIDES AND ALKALI METAL RHODANIDES

2019 ◽  
Vol 16 (32) ◽  
pp. 996-1009
Author(s):  
R. N. ZHANALIYEVA ◽  
B. B. TORSYKBAYEVA ◽  
M. O. ALTYNBEKOVA ◽  
B. S. IMANGALIYEVA ◽  
A. Zh. NAZAROVA
Keyword(s):  
Nucleophilic Substitution ◽  
Chlorine Atom ◽  
Diethylene Glycol ◽  
Reaction Centers ◽  
Hydroxyl Group ◽  
Primary Role ◽  
Substitution Reactions ◽  
Electrophilic Reagents ◽  
Carbonic Acids ◽  
Acyloxy Group

This work is aimed at studying the reaction of nucleophilic substitution of the chlorine atom in 2-(2'-acyloxy-ethoxy) ethylchlorides with amines and a rhodanide ion and developing methods of synthesizing a 2-(2'-acyloxy-ethoxy) ethylchlorides, rhodanides, and their derivatives previously unknown in specialized literature. In the chlorohydrin molecule of diethylene glycol, there are two reaction centers that allow carrying out nucleophilic substitution reactions, as well as reactions that promote them with electrophilic reagents. The authors carried out several experiments for acylating diethylene glycol chlorohydrine with carbonic acids, reactions of nucleophilic substitution of the chlorine atom in 2-(2'-acyloxy-ethoxy) ethylchlorides with various amines as well as synthesized the chloracetoxyethyl ether of rhodane acetic acid. While studying the nucleophilic substitution of 2-(2'-acyloxy-ethoxy) ethylchlorides with the rhodanide ion, it was discovered that only the chlorine atom was replaced. The possibility of the nucleophilic substitution of the ethylene chlorohydrine was shown by the example of N-methyl and N-ethylanilines. It was discovered that the hydroxyl group of diethylene glycol could react with carbonic acids in the presences of catalysts and, therefore, encourage esterification. It has been found out that the nucleophilic substitution of the chlorine atom in 2-(2'-acyloxy-ethoxy) ethylchlorides with the rhodanide ion goes smoothly in the presence of potassium iodide acting as an activator and that the acyloxy group is unaffected. It has been discovered that the primary role in the nucleophilic substitution of alcoxyalkylhalides is played by the basicity of amines and the essence and position of substituents relative to the alcoxyl group of the haloid atom.

ChemInform Abstract: Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer.

ChemInform ◽  
2016 ◽  
Vol 47 (25) ◽  
Author(s):  
Anon Bunrit ◽  
Christian Dahlstrand ◽  
Pemikar Srifa ◽  
Sandra K. Olsson ◽  
Genping Huang ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Hydroxyl Group ◽  
Chirality Transfer
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