Intramolecular Diels-Alder reaction of .alpha.,.beta.-unsaturated ester dienophiles with cyclopentadiene and the dependence on tether length

1989 ◽  
Vol 54 (2) ◽  
pp. 434-444 ◽  
Author(s):  
John R. Stille ◽  
Robert H. Grubbs
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Unsaturated Ester ◽  
Diels Alder Reaction ◽  
Alpha Beta

scholarly journals 1,5-Dichloroethanoanthracene Derivatives as Antidepressant Maprotiline Analogues: Synthesis and DFT Computational Calculations

2021 ◽  
Author(s):  
Mujeeb Sultan ◽  
Renjith Raveendran Pillai ◽  
Eman Alzahrani
Keyword(s):  
Density Functional ◽  
Density Functional Theory Calculations ◽  
Intermediate Compound ◽  
2D Nmr ◽  
Alder Reaction ◽  
Diels Alder ◽  
Experimental Result ◽  
Unsaturated Ester ◽  
Diels Alder Reaction ◽  
Computational Calculations

Abstract The chlorinated tetracyclic 1,5-dichloro-9,10-dihydro-9,10-ethanoanthracen-12-yl)-N-methylmethanamine 1, a maprotiline analogue, has been synthesized via reduction and Diels–Alder reaction followed by reductive amination of Aldehyde 2. Density Functional Theory calculations were performed to identify the possible isomers of the intermediate compound aldehyde 2, these calculations were in a good agreement with experimental result where aldehyde 2 could exist in three isomers with comparable energies. In addition, the side chain of this aldehyde 2 was extended via Wittig reaction to obtain the unsaturated ester 5 that subjected to selective olefinic catalytic hydrogenation to obtain the corresponding saturated ester 6. 1D-NMR (DEPT) and 2D-NMR (HSQC, DQF-COSY) techniques were recruited for structural elucidation in addition to HRMS.

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction
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