Norbornadiene (3) reacts with 1,1-dimethyldiazenium bromide (1) in 1.5 M hydrobromic acid to give 52 % of the entfo-A-dimethylaminoaziridine (6), 4% of the other endo product 7, and 39 % of 8, 9,10, and 11, nortricyclene products of exo attack. The relative yields of 7-11 are greater with increasing hydrobromic acid concentrations, and that of 6 diminishes. Endo addition to such an extent is attributed to preliminary 2,6 cycloaddition of 1 to 3, and it has been shown to be reversible. Norbornene 2 also gives the aziridine 4 (here the exo isomer) and 5. The reaction of 4 with hydrobromic acid has been shown to give 5. «ifo-5-Norbornene-2-methanol gives 13, and benzonorbornadiene gives 14, products expected from their prior electrophilic additions. n hydrobromic acid 1,1-dimethyldiazenium bromide(1) adds like a dienophile to 1,3-alkadienes1 and like an electrophile with some styrenes,lb but it does not react with ordinary olefins. However, such reactions occur with the more reactive bicyclic olefins.
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