The High Pressure Diels-Alder Reactions of an Acylated Quinone Imine Ketal; A 3-Aminobenzyne Equivalent

Synlett ◽  
1995 ◽  
Vol 1995 (11) ◽  
pp. 1165-1167 ◽  
Author(s):  
Michael A. Kerr
Keyword(s):  
High Pressure ◽  
Quinone Imine ◽  
Diels Alder

scholarly journals Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

2015 ◽  
Vol 11 ◽  
pp. 576-582 ◽  
Author(s):  
Grzegorz Mlostoń ◽  
Paulina Grzelak ◽  
Maciej Mikina ◽  
Anthony Linden ◽  
Heinz Heimgartner
Keyword(s):  
High Pressure ◽  
Room Temperature ◽  
Thermal Conditions ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hydrogen Shift ◽  
Diels Alder Reaction ◽  
Shift Sequence

Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

ChemInform Abstract: The High Pressure-Mediated Intramolecular Diels-Alder Reaction of Furans: Factors Controlling Cycloaddition with Monoactivated Dienophiles.

ChemInform ◽  
1989 ◽  
Vol 20 (14) ◽  
Author(s):  
L. M. HARWOOD ◽  
S. A. LEEMING ◽  
N. S. ISAACS ◽  
G. JONES ◽  
J. PICKARD ◽  
...  
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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