Journal of Organic Chemistry p. 3036 - 3040 (1981)
Update date:2022-08-05
Topics:
Rammash, Bahlul Kh.
Gladstone, C.M.
Wong, John L.
The reaction of the title azadiene 1 with cyclopentadiene via the ene moiety of 1 as the dienophile yielded 5 quantitatively.Chlorination of 5 gave rise to a single dichloro derivative 6.The cycloadduct 7, obtained from reacting cyclopentene with 1, was found to be different from 9, the hydrogenation product of 5, thus eliminating any product which requires 1 behaving as diene.Also, the use of 15N label in the sequence rules out 5a, an imine isomer, as a candidate.However, the existence of the diene character of 1 in reaction with a conjugated diene was found upon heating 1 with cyclohexadiene.Two adducts were isolated in a ratio of 4:1.The minor product was assigned structure 12 which is similar to 5 derived from 1.The cyclohexene adduct of 1 was found to be identical with 14, the dihydro derivative of the major adduct from cyclohexadiene.The latter is assigned structure 10, analogous to the regiospecific formation of endo-5-substituted-2-azanorbornenes from 1 and olefins such as styrene.In the case of an acyclic diene addend such as trans-piperylene, 1 behaves only as a diene, yielding the adduct 16 only.It appears that the steric factor is an important one in deciding the diene or dienophilic reactivity of 1.
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