Abstract
The reactions between 1,4-bis(diethylamino)-2,3-dinitro-1,3-butadiene (2), easily obtainable by ring-opening of 3,4-dinitrothiophene with diethylamine, and 2-substituted vinylmagnesium bromides gave good yields of the 4,5-dinitro-1,3,5,7-octatetraene derivatives 3a–e. With 1-phenylmagnesium bromide, conversely, only 3,4-dinitro-1,4-diphenyl-1,3,5-cyclooctatriene (4f) was obtained. From the unsubstituted dinitrooctatetraene 3a both the octatriene cycloisomer 4a and the valence tautomer of the latter (6a) could be isolated and characterized. The results obtained evidence an unfavourable effect of the two nitro groups on the cycloisomerization process of the octatetraene system.
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