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                    The Effect of p-Bond Screening on the Reaction of s-Tetrazines with 7-Substituted Benzonorbornadienes
                
                                    
                
                
                    Published:
11 September 2000
by MDPI
in The 4th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
                
                                    
                
                
                    Abstract: Benzonorbornadiene 21, 7-spirocyclopropylbenzonorbornadiene 23, 7,7-dimethylbenzonorbornadiene 25 , and 7-spirocyclopentylbenzonorbornadiene 27 have been reacted with 3,6-di(2-pyridyl)-s-tetrazine (21>23>25=27) to form symmetrical 4,5-hydropyridazines which are stable towards fragmentation but rearrange with varying facility to their 1,4 isomers. The facial selectivity of attack on the p-bond changes from exo-attack for 21 and 23 to endo-attack for 25 and 27. The 7-spirocyclopropylbenzonorbornadiene 23 typically forms a mixture of dihydropyridazines with exo-stereochemistry, which undergo further stereochemical isomerisation to an exo-fused product upon acetylation (acetyl chloride in hot pyridine). Oxidation with DDQ of these dihydro compounds individually or as mixtures gives the corresponding fused 3,6-dipyridylpyridazines
                
                                    
                        Keywords: n/a
                    
                
                
                
                 
            
 
        
    
    
         
    
    
         
    
    
         
    
    
         
    
 
                                