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Cycloaddition Reactions of α-Chloroalkylideneamine Oxides with Hetero-enes, I; Carbonyl Compounds
Neidlein, Richard,Shatzmiller, Shimon,Walter, Eckardt
, p. 686 - 692 (2007/10/02)
Cycloaddition reaction of N-(2-chloroethylidene)cyclohexylamine oxide (2) with the hetero-enes 1a-1f at 10 deg C in the presence of AgBF4 in 1,2-dichloroethane as solvent furnishes the reactive, dipolar intermediate iminium salts 3a-3f.Subsequent reduction of 3a-3f in water by NaBH4 yields the substituted 1,3-dioxa-4-azacyclohexanes 4a-4f.From the bicyclic "hetero-ene" camphor (5) and from cholestanone (8) the spirocyclic compounds 7 and 9 have been obtained in an analogous way. - On the other hand, reaction of the hetero-enes 1c, 1e, 1f, and cyclododecanone (11) with 2 in the presence of AgBF4 give the iminium salts 3c, 3e, 3f and 12 which, in aquous 10percent KCN solution, yield the nitriles 10a-10c and 13 as mixtures of their isomers.
