Bulletin of the Chemical Society of Japan p. 1921 - 1924 (1990)
Update date:2022-08-03
Topics:
Tokumitsu, Takao
The reaction of 2-(nitromethylene)imidazolidine (1) with olefins bearing an electron-withdrawing group gave Michael-type addition products and/or 5-nitro-1,7-diazabicyclo<4.3.0>nonane derivatives derived from the Michael-type adduct.The reaction of 1 with α,β-unsaturated aldehydes in the presence of an acid, on the other hand, gave similar diazabicyclic derivatives and 2-<(2-imidazolidinylidene)nitromethylene>-5-nitro-1,7-diazabicyclo<4.3.0>non-5-ene derivatives.The reaction of 1 with saturated and aromatic aldehydes in the presence of hydrochloric acid gave 1,3-bis(2-imidazolidinylidene)-1,3-dinitropropane derivatives.The enhanced enaminic character of 1 is ascribable to the two electron-donating amino groups fixed in a five-membered ring.
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