Abstract
In this paper we describe the synthesis of a γ,δ-unsaturated aldehyde from a bicyclic Diels-Alder adduct, to be used in future electrocyclic reaction studies. A number of reactions produced undesired materials resulting from the interaction between functions, forcing the use of partial protection to accomplish a synthesis that would be otherwise straightforward. Suggestions to account for the results are given.
Highlights
During our studies on the preparation of polycyclic compounds through the Diels-Alder reactions we have faced a circumstance of unusual recurrence of interference between two functions existing in the same molecule, resulting in changes of the properties usually associated with each function and giving rise to unexpected and rather surprising results
The relatively simple synthesis of compound 2a here described shows the importance of taking into account the intramolecular interactions between two functions, even in simple molecules, and how valuable the use of protective groups can be to overcome this sort of problems
As compound 13 is formed in only 5 % yield, this reaction is obviously less important
Summary
During our studies on the preparation of polycyclic compounds through the Diels-Alder reactions we have faced a circumstance of unusual recurrence of interference between two functions existing in the same molecule, resulting in changes of the properties usually associated with each function and giving rise to unexpected and rather surprising results.In our view, it is essential to improve the systematization of knowledge about interferences between functions, bringing higher reliability to organic syntheses projects. Treatment of 1 with PBr3, led to a surprising result: after hydrolysis and extraction, a phosphite of the diol was obtained as a mixture of stereoisomers that were separated by column chromatography (compounds 7a and 7b).
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