Microwave-Enhanced Organic Syntheses for the Undergraduate Laboratory: Diels−Alder Cycloaddition, Wittig Reaction, and Williamson Ether Synthesis

2010 ◽  
Vol 87 (1) ◽  
pp. 84-86 ◽  
Author(s):  
Marsha R. Baar ◽  
Danielle Falcone ◽  
Christopher Gordon
Keyword(s):  
Wittig Reaction ◽  
Diels Alder ◽  
Organic Syntheses ◽  
Undergraduate Laboratory ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis

scholarly journals Unexpected course of a Williamson ether synthesis

ARKIVOC ◽  
2006 ◽  
Vol 2007 (7) ◽  
pp. 291-300
Author(s):  
Klaus-Peter Zeller ◽  
Peter Haiss ◽  
Meike Hartmann ◽  
Klaus Eichele
Keyword(s):  
Ether Synthesis ◽  
Williamson Ether Synthesis

scholarly journals Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 673 ◽  
Author(s):  
Feiyue Hao ◽  
Nagatoshi Nishiwaki
Keyword(s):  
Nitro Group ◽  
Functional Groups ◽  
Recent Progress ◽  
Alder Reaction ◽  
Diels Alder ◽  
Organic Syntheses ◽  
Diels Alder Reaction ◽  
Direct Functionalization ◽  
Nucleophilic Reagents

Nitro group is one of the most important functional groups in organic syntheses because its strongly electron-withdrawing ability activates the scaffold, facilitating the reaction with nucleophilic reagents or the Diels–Alder reaction. In this review, recent progress in the nitro-promoted direct functionalization of pyridones and quinolones is highlighted to complement previous reviews.

C -Nucleosides and Related Compounds. IV. The Synthesis and Chemistry of D,L-2,5-Anhydroallose Derivatives

1975 ◽  
Vol 53 (1) ◽  
pp. 131-137 ◽  
Author(s):  
George Just ◽  
Alain Martel ◽  
Karl Grozinger ◽  
Mohabir Ramjeesingh
Keyword(s):  
Wittig Reaction ◽  
Diels Alder ◽  
Free Aldehyde ◽  
Related Compounds ◽  
Alder Adduct

Methyl β-nitroacrylate (1) reacted with furan to give the corresponding Diels–Alder adduct, which was converted to D,L-3,4-di-O-isopropylidene-2,5-anhydroallose (9) in a five-step sequence in 14% yield, based on 1. The conversion of 9 to its oxime, semicarbazone, and thiosemi-carbazone is described, as well as the synthesis of the free aldehyde 15, and of the Wittig reaction product 14.

Dimethyl sulfoxide as a solvent in the Williamson ether synthesis

1969 ◽  
Vol 47 (11) ◽  
pp. 2015-2019 ◽  
Author(s):  
Russel G. Smith ◽  
Alan Vanterpool ◽  
H. Jean Kulak
Keyword(s):  
Reaction Time ◽  
Dimethyl Sulfoxide ◽  
Butyl Alcohol ◽  
Major Product ◽  
Hydroxyl Groups ◽  
Reaction Products ◽  
Butyl Chloride ◽  
Butyl Ether ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis

Using the conventional Williamson ether synthesis, n-butyl ether was prepared from sodium hydroxide, n-butyl alcohol, and n-butyl chloride using excess of the alcohol as solvent in 61% yield after 14 h reaction time. However, when the excess alcohol was replaced by dimethyl sulfoxide, the yield of ether rose to 95% with 9.5 h reaction time. Other primary alkyl chlorides exhibited similar behavior to n-butyl chloride, but secondary alkyl chlorides and primary alkyl bromides gave little etherification, elimination being the major reaction. Unreactive halides, such as vinyl chloride, phenyl bromide, and 2,4-dinitrobromobenzene, were not etherified in dimethyl sulfoxide. The reaction products obtained from aliphatic dichlorides depended upon the relative positions of the chlorine atoms. Secondary alcohols reacted to give ethers, but tertiary alcohols were very unreactive. Polyols generally gave high yields of ethers, the major product being that in which all but one of the hydroxyl groups became etherified. Under forcing conditions, however, completely etherified polyols could be obtained.

Williamson Ether Synthesis on Solid Support:  Substitution versus Elimination

2001 ◽  
Vol 3 (2) ◽  
pp. 154-156 ◽  
Author(s):  
Avi Weissberg ◽  
Adi Dahan ◽  
Moshe Portnoy
Keyword(s):  
Solid Support ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis
Sign in / Sign up

Export Citation Format

Share Document