Reactions of Dimethyl (2'-Oxopropylidene)Propanedioate and Dimethyl (3'-Bromo-2'-oxopropylidene)propanedioate, Two Highly Electrophilic Trisubstituted Alkenes

1987 ◽  
Vol 40 (11) ◽  
pp. 1831 ◽  
Author(s):  
DW Cameron ◽  
RW Read ◽  
J Stavrakis
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Low Molecular Weight ◽  
Ene Reaction ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Alkaline Conditions ◽  
Nucleophilic Reagents ◽  
Trisubstituted Alkenes ◽  
Electron Demand

The keto diester, dimethyl (2'-oxopropylidene)propanedioate, and its new 3'-bromo derivative have been made to react with a variety of nucleophilic reagents. Low molecular weight products have been obtained efficiently by processes involving conjugate addition, Diels-Alder reaction, Diels-Alder reaction having inverse electron demand, or ene reaction. Regiochemistry of the reactions is controlled by the dominant withdrawing effect of the two geminal ester groups. The amine addition products of the bromo keto diester were found to undergo a novel secondary dehydrobromination reaction under alkaline conditions.

Single wall carbon nanotube (SWCNT)–gold nanorod (AuNR) conjugates via thermally-mild reaction conditions

2017 ◽  
Vol 41 (21) ◽  
pp. 12392-12396 ◽  
Author(s):  
Siting Ni ◽  
Jun Zhu ◽  
Mohamed Amine Mezour ◽  
R. Bruce Lennox
Keyword(s):  
Carbon Nanotube ◽  
Covalent Binding ◽  
Alder Reaction ◽  
Diels Alder ◽  
Gold Nanorod ◽  
Reaction Conditions ◽  
Single Wall Carbon ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

A thermally-mild method for covalent binding of SWCNTs to AuNRs, based on an inverse-electron-demand Diels–Alder reaction, is established and discussed.

Total syntheses of ericifolione and analogues via a biomimetic inverse-electron-demand Diels-Alder reaction

2021 ◽  
Author(s):  
Tingting Zhou ◽  
Anquan Zheng ◽  
Luqiong Huo ◽  
Changgeng Li ◽  
Haibo Tan ◽  
...  
Keyword(s):  
Sodium Acetate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Total Syntheses ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Sterically Hindered ◽  
Electron Demand

Driven by bioinspiration and appreciation of the structure of ericifolione, a biomimetic tautomerization/intermolecular inverse-electron-demand hetero Diels-Alder reaction cascade sequence promoted by sodium acetate to rapidly construct sterically hindered dihydropyran scaffolds...

Synthesis of 6H-Dibenzo[b,d]pyran-6-ones Using the Inverse Electron Demand Diels–Alder Reaction

2011 ◽  
Vol 76 (21) ◽  
pp. 9015-9030 ◽  
Author(s):  
Ian R. Pottie ◽  
Penchal Reddy Nandaluru ◽  
Wendy L. Benoit ◽  
David O. Miller ◽  
Louise N. Dawe ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand
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