102244-87-1

Upstream product

• 1816-92-8 Methyl azidoacetate 
• 83-38-5 2,6-dichlorobenzaldehyde 

Downstream Products

• 102245-07-8 2,6-Dichlor-α-amino-zimtsaeuremethylester 
• 102244-96-2 trans-2,6-Dichlor-α-(N,N-diacetylamino-)-zimtsaeuremethylester 
• 102244-95-1 cis-2,6-Dichlor-α-(N,N-diacetylamino-)-zimtsaeuremethylester 
• 98081-82-4 methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate 

Relevant academic research and scientific papers

Methyl 2-aryl-2H-azirine-3-carboxylates as dienophiles

Diels-Alder reactions of the methyl 2-aryl-2H-azirine-3-carboxylates 1a and 1b have been investigated in order to determine the stereoselectivity and regioselectivity of the reaction. The azirines react with a range of electron rich dienes at room temperature to give Diels-Alder adducts. The reaction leads to the formation of endo-cycloadducts with both cyclic and acyclic dienes; furan Is exceptional in giving an exo-adduct 7. X-Ray crystallography has established the structure 9 of the Diels-Alder adduct formed from the azirine 1a and 1-acetoxybutadiene. The same regioselectivity, in which the more nucleophilic terminus of the diene combines with the carbon atom of the C=N bond, is found in the adducts from several other 1- and 2-substituted dienes. Only isoprene, among the dienes examined, gives a mixture containing the opposite regioisomer 14 as a minor component.