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Several new N‐allyl‐N‐(5‐substituted)‐2‐furfuryl‐p)‐toluidines IIIa‐e with Cl, Br, I, NO2 or CH3O groups in position 5 of the furan nucleus were prepared by allylation of the corresponding secondary furfurylaryl‐amines. Both, electron withdrawing and releasing substituents enhanced the yield of intramolecular [4+2] cycloaddition.

The electron impact induced fragmentations of the C-5 unsubstituted and 5-methyl N-aryl-4H-5,7a-epoxyisoidoünes (where aryl is phenyl, p-tolyl, p-methoxyphenyl, o -methoxyphenyl and p-chlorophenyl) were investigated. The fragmentation pattems deduced were supported by exact mas measnrements of prominent ions and by deutenum labelling. The retro Diels-Alder fragmentation h e d out to be a predominant process in all the compounds investigated. Ĩ I the mass spectra of the 5-methyl N-aryl-4H-5,7a-epoxyisollidoün~ hydrogen migration preceding fragmentation occorred. From the mam speetnun of the spedeally deuterated componnd it was concluded that the transferred hydrogen onginates exeiuSive1y from the 5-methyi group.

Die Azomethine (I) werden zu den Aminen (II) reduziert, die in die Thioharnstoffe (III) (keine Aush‐Angaben) und die tert.‐ Amine (IV) übergeführt werden.

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