1,1′,3,3′-Tetraalkyl-2,2′-biperimidinylidenes: Unexpected Substituent Effects on the Reactivity of Carbon—Carbon Double Bond.

ChemInform ◽  
2003 ◽  
Vol 34 (20) ◽  
Author(s):  
Buelent Alici ◽  
Tuncer Hoekelek ◽  
Engin Cetinkaya ◽  
Bekir Cetinkaya
Keyword(s):  
Double Bond ◽  
Substituent Effects ◽  
Carbon Double Bond

1,1′,3,3′-Tetraalkyl-2,2′-biperimidinylidenes: Unexpected substituent effects on the reactivity of carbon-carbon double bond

2003 ◽  
Vol 14 (1) ◽  
pp. 82-87 ◽  
Author(s):  
Bülent Alıcı ◽  
Tuncer Hökelek ◽  
Engin Çetinkaya ◽  
Bekir Çetinkaya
Keyword(s):  
Double Bond ◽  
Substituent Effects ◽  
Carbon Double Bond

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.

Cycloaddition reactions across the carbon-carbon double bond of thiirene 1,1-dioxide

1984 ◽  
Vol 49 (7) ◽  
pp. 1300-1302 ◽  
Author(s):  
Mitsuo Komatsu ◽  
Yasuo Yoshida ◽  
Masatoshi Uesaka ◽  
Yoshiki Ohshiro ◽  
Toshio Agawa
Keyword(s):  
Double Bond ◽  
Cycloaddition Reactions ◽  
Carbon Double Bond
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