Difluorocarbene induced facile synthesis of chlorohydrins from glycidyl ethers

2004 ◽  
Vol 82 (8) ◽  
pp. 1249-1253 ◽  
Author(s):  
Sapna Singh ◽  
Pinaki S Bhadury ◽  
Mamta Sharma ◽  
Meehir Palit ◽  
Devendra K Jaiswal
Keyword(s):  
Key Words ◽  
Ring Opening ◽  
High Yield ◽  
Facile Synthesis ◽  
Glycidyl Ethers ◽  
Ring Opening Of Epoxides

A novel and unusual approach based on a ClCF2COONa–DMF system has been developed for the synthesis of chlorohydrins via an unexpected mechanism. In a first ever report for the synthesis of chlorohydrins from glycidyl ethers, e.g., CH2=CH-CH2-O-Z, CH3CH2-O-Z, C6H5-O-Z, C6H4(o-CH3)-O-Z, CH2=C(CH3)C(=O)-O-Z, etc., (where Z = glycidyl), difluorocarbene-induced facile regioselective ring opening of epoxides has generated the compound in high yield (70%–83%). [Formula: see text] Key words: difluorocarbene, sodium chlorodifluoroacetate, chlorohydrins.

Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides

Synthesis ◽  
2019 ◽  
Vol 51 (10) ◽  
pp. 2214-2220 ◽  
Author(s):  
Monika Stefaniak ◽  
Jarosław Romański
Keyword(s):  
Click Chemistry ◽  
Ring Opening ◽  
Facile Synthesis ◽  
Step Procedure ◽  
Ring Opening Of Epoxides ◽  
One Step ◽  
Thiacrown Ethers ◽  
Hydroxy Groups ◽  
First Time ◽  
Nucleophilic Ring Opening

The title thiacrown ethers were prepared in a one-step procedure to give a series of unique macrocycles possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson’s birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared for the first time.

scholarly journals Regioselective Ring Opening of Epoxides with Amines Using Silica-bonded S-sulfonic Acid under Solvent-free Conditions

2017 ◽  
Vol 56 (4) ◽  
Author(s):  
Mahmood Tajbakhsh ◽  
Rahman Hosseinzadeh ◽  
Parizad Rezaee ◽  
Heshmatollah Alinezhad
Keyword(s):  
Ring Opening ◽  
Sulfonic Acid ◽  
Room Temperature ◽  
Amino Alcohols ◽  
Solvent Free ◽  
High Yield ◽  
Reusable Catalyst ◽  
Solvent Free Conditions ◽  
Ring Opening Of Epoxides

Silica-bonded S-sulfonic acid (SBSSA) was used as a recyclable and reusable catalyst for the synthesis of β-amino alcohols. Several amines were reacted with epoxides to afford regioselective β-amino alcohols in high yield under solvent-free conditions at room temperature.

Bi(OTf)3-catalyzed Regioselective Ring Opening of Epoxides with Phenols: Facile Synthesis of 1,3-Diaryloxy-2-propanols

2005 ◽  
Vol 34 (8) ◽  
pp. 1142-1143 ◽  
Author(s):  
Ahmed Kamal ◽  
Syed Kaleem Ahmed ◽  
Mahendra Sandbhor ◽  
Mohammed Naseer Ahmed Khan ◽  
Mohammed Arifuddin
Keyword(s):  
Ring Opening ◽  
Facile Synthesis ◽  
Ring Opening Of Epoxides

Bi(OTf)3-Catalyzed Regioselective Ring Opening of Epoxides with Phenols: Facile Synthesis of 1,3-Diaryloxy-2-propanols.

ChemInform ◽  
2006 ◽  
Vol 37 (1) ◽  
Author(s):  
Ahmed Kamal ◽  
Syed Kaleem Ahmed ◽  
Mahendra Sandbhor ◽  
Mohammed Naseer Ahmed Khan ◽  
Mohammed Arifuddin
Keyword(s):  
Ring Opening ◽  
Facile Synthesis ◽  
Ring Opening Of Epoxides
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