Nucleophilic Reactivity of the Carbon-Carbon Double Bond. I. Solvolytic Ring Closure of 2-(Δ3-Cyclopentenyl)ethyl and 1-(Δ3-Cyclopentenyl)-2-propyl Arenesulfonates

1965 ◽  
Vol 87 (6) ◽  
pp. 1288-1297 ◽  
Author(s):  
Paul D. Bartlett ◽  
Shelton Bank ◽  
Robert J. Crawford ◽  
George H. Schmid
Keyword(s):  
Double Bond ◽  
Ring Closure ◽  
Carbon Double Bond ◽  
Nucleophilic Reactivity

Nucleophilic reactivity of the carbon-carbon double bond—V

Tetrahedron ◽  
1966 ◽  
Vol 22 ◽  
pp. 399-420 ◽  
Author(s):  
P.D. Bartlett ◽  
E.M. Nicholson ◽  
R. Owyang
Keyword(s):  
Double Bond ◽  
Carbon Double Bond ◽  
Nucleophilic Reactivity

Nucleophilic reactivity of the carbon-carbon double bond. VI. The use of urea as a base in acetolysis reactions

1967 ◽  
Vol 32 (1) ◽  
pp. 150-153 ◽  
Author(s):  
Walter S. Trahanovsky ◽  
Michael P. Doyle ◽  
Paul Doughty Bartlett
Keyword(s):  
Double Bond ◽  
Carbon Double Bond ◽  
Nucleophilic Reactivity

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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