Synthesis of Two 2,2′-Bipyridine Containing Macrocycles for the Preparation of Interlocked Architectures

2017 ◽  
Vol 70 (5) ◽  
pp. 588 ◽  
Author(s):  
Jacob Whittaker ◽  
Suresh Moorthy ◽  
Jonathan Cremers ◽  
Jason R. Price ◽  
John C. McMurtrie ◽  
...  
Keyword(s):  
Sodium Borohydride ◽  
High Yield ◽  
Oligomer Formation ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis

The synthesis and characterisation of two 28-membered, 2,2′-bipyridine-containing macrocycles in high yield is reported. The first imine-containing macrocycle was formed via a Williamson ether synthesis and showed no evidence of higher oligomer formation. Reduction of the imines with sodium borohydride produced the second macrocycle quantitatively.

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

Flavan derivatives. XXIII. Preparation and synthetic applications of Flav-3-enes

1968 ◽  
Vol 21 (9) ◽  
pp. 2247 ◽  
Author(s):  
JW Clark-Lewis ◽  
RW Jemison
Keyword(s):  
Sodium Borohydride ◽  
Acidic Medium ◽  
Catalytic Reduction ◽  
Heterocyclic Ring ◽  
High Yield ◽  
Lithium Aluminium Hydride ◽  
Lower Field ◽  
Field Characteristic ◽  
Lithium Aluminium ◽  
New Synthesis

2'-Hydroxychalcones and α-alkoxy-2'-hydroxychalcones are converted by sodium borohydride in isopropanol into flav-3-enes and 3-alkoxyflav-3-enes in the convenient new synthesis which makes these flavenes readily available. Catalytic reduction of the flavenes gives the corresponding flavans or 3-alkoxyflavans in high yield, and the latter are obtained mainly in the 2,s-cis-form. The flavenes immediately give flavs lium cations in the cold when treated with acids in air, and oxidation of 5,7,3',4'-tetramethoxyflav-3-ene with benzoquinone in an acidic medium gave the flavylium salt, isolated as the ferrichloride. Reduction of 5,7,3',4'-tetramethoxy-flavylium chloride with lithium aluminium hydride gave 5,7,3',4'-tetramethoxy-flav-2-ene identical with the flavene obtained from (-)-epicatechin tetramethyl ether, and confirms an earlier investigation by Gramshaw, Johnson, and King. In its N.M.R. spectrum the heterocyclic-ring protons of this flav-2-ene give an ABX multiplet which is easily distinguished from the ABX multiplet at much lower field characteristic of flav-3-enes.

Reductions with sulfurated borohydrides. V. Reductions of ketones

1970 ◽  
Vol 48 (15) ◽  
pp. 2366-2371 ◽  
Author(s):  
J. M. Lalancette ◽  
A. Freche
Keyword(s):  
High Temperature ◽  
Carbonyl Group ◽  
Sodium Borohydride ◽  
Room Temperature ◽  
High Yield ◽  
High Yields ◽  
Very High

Ketones can be reduced with sulfurated sodium borohydride. Very high yield (≈90%) of the corresponding alcohol is obtained with the appropriate ratio of ketone and hydride at room temperature. The reaction is much influenced by the steric environment around the carbonyl group. At high temperature (65°) disulfides and tetrasulfides are produced. In some cases the structure of those sulfides have been established. Conjugated ketones can be reduced to the corresponding alcohols with very high yields.

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

Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β‐Keto Esters

2015 ◽  
Vol 21 (40) ◽  
pp. 14095-14098 ◽  
Author(s):  
Kazutaka Shibatomi ◽  
Manato Kotozaki ◽  
Nozomi Sasaki ◽  
Ikuhide Fujisawa ◽  
Seiji Iwasa
Keyword(s):  
Keto Esters ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis
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