605671-95-2

Upstream product

• 492449-46-4 methyl 2,2-dimethyl-4,4-diphenyl-3-butenoate 
• 110835-94-4 2,2-dimethyl-4,4-diphenylbut-3-enoic acid 
• 1027373-32-5 2,2-dimethyl-4,4-diphenyl-3-butenoyl chloride 

Downstream Products

• 605671-96-3 1,1-dimethyl-3,3-diphenyl-2-propenyl isocyanate 
• 605671-92-9 1,1-dimethyl-3,3-diphenyl-2-propenylamine 
• 605671-70-3 (E)-3,3-dimethyl-1,5,5-triphenyl-2-aza-1,4-pentadiene 
• 605672-08-0 N-benzhydryl-1,1-dimethyl-3,3-diphenyl-2-propenylamine 
• 605671-76-9 3,3-dimethyl-1,1,5,5-tetraphenyl-2-aza-1,4-pentadiene 

Relevant academic research and scientific papers

Novel photoreactions of 2-Aza-1,4-dienes in the triplet excited state and via radical-cation intermediates. 2-Aza-di-π-methane rearrangements yielding cyclopropylimines and N-vinylaziridines

Triplet-sensitized irradiation of 2-aza-1,4-dienes affords N-cyclopropylimines via 2-aza-di-π-methane (2-ADPM) rearrangement pathways. In the case of the pentaphenyl-substituted azadiene 1, irradiation leads to formation of cyclopropylimine 2 as well as N-vinylaziridine 3. The transformations represent the first examples of di-π-methane rearrangement reactions that yield three-membered heterocyclic products. SET-sensitized irradiation of 2-aza-1,4-dienes, by using 9,10-dicyanoanthracene (DCA) as an electron-acceptor sensitizer and biphenyl as cosensitizer, brings about regioselective formation of N-vinylaziridines. Under these conditions, azadiene 1 also affords cyclopropylimine 37, resulting from an aryl-di-π-methane rearrangement. This result demonstrates that di-π-methane reactions can also take place via radical-cation intermediates. In some instances, imine and olefin centered cation-radical intermediates, generated by SET-sensitized irradiation, undergo alternative reactions to produce isoquinoline and benzoazepine products.