Synthesis of conjugated dienes and polyenes via diethyl phosphite promoted carbonyl olefination

RSC Advances ◽  
2014 ◽  
Vol 4 (74) ◽  
pp. 39497-39507 ◽  
Author(s):  
Ru Wang ◽  
Songlin Zhang
Keyword(s):  
Conjugated Dienes ◽  
Diethyl Phosphite ◽  
Double Bonds ◽  
One Pot ◽  
Carbonyl Olefination

A convenient one-pot protocol involving the transfer of carbon–carbon double bonds to obtain conjugated dienes and polyenes has been developed.

An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1437-1441
Author(s):  
Xu yan Cao ◽  
Fei Huang ◽  
Songlin Zhang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Type Reaction ◽  
Mild Conditions ◽  
Allyl Halides ◽  
Barbier Reaction

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3446-3451
Author(s):  
Songlin Zhang ◽  
Dengbing Xie ◽  
Yiqiong Wang ◽  
Bo Yang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
Carbon Double Bond ◽  
Allyl Halides ◽  
First Time

The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

Monoozonides of chloro-substituted conjugated dienes: preparation, stability, and some chemical reactions

1986 ◽  
Vol 64 (8) ◽  
pp. 1553-1559 ◽  
Author(s):  
Karl Griesbaum ◽  
Ashis R. Bandyopadhyay ◽  
Martin Meister
Keyword(s):  
Chemical Reactions ◽  
Conjugated Dienes ◽  
Double Bonds ◽  
Subsequent Reaction

The chlorodienes (E)-4-chloro-3-methyl-1,3-hexadiene (5a), (E)- and (Z)-4-chloro-2,3-dimethyl-1,3-hexadiene (5b/6b), (E,E)-5-chloro-4-methyl-2,4-heptadiene (5c), (4E)- and (4Z)-5-chloro-3,4-dimethyl-2,4-heptadiene (5d/6d), chloroprene (11a), and 2-chloro-3-methyl-1,3-butadiene (11b) are selectively ozonized at the non-chlorinated double bonds to give the corresponding monoozonides 7, 8, and 12. Further ozonolyses of the monoozonides of 5b and of 11b in methanol as well as epoxidation of the monoozonide of 5b and subsequent reaction of the resulting chloroepoxide with AgBF4 are described.

scholarly journals A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

2014 ◽  
Vol 10 ◽  
pp. 722-731
Author(s):  
Natalia V Pavlenko ◽  
Tatiana I Oos ◽  
Yurii L Yagupolskii ◽  
Igor I Gerus ◽  
Uwe Doeller ◽  
...  
Keyword(s):  
Amino Acids ◽  
Ethyl Ester ◽  
Nucleophilic Addition ◽  
Phosphinic Acid ◽  
Double Bonds ◽  
Synthetic Methodology ◽  
One Pot ◽  
Phosphinic Acids

A series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of proteinogenic and nonproteinogenic α-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds.

Sign in / Sign up

Export Citation Format

Share Document