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Synthesis and Reactions of N-Silylated Ene-diamines, II. - Cycloadditions: Synthesis of Derivatives of 1,4-Diamino-1,3-butadiene-2,3-dicarboxylic Acid
Dieck, Heindirk tom,Zettlitzer, Michael
, p. 795 - 802 (2007/10/02)
From 1,4-diaza-1,3-dienes 1, alkali metals, and corresponding chlorosilanes 1,3-diaza-2-sila-4-cyclopentenes 2, acyclic analogues 3, and also a spiro-bis(enediamine) 4 are obtained.Compounds 2 contain a reactive, electron-rich C=C-double bond, to which tetracyanoethylene adds rapidly.Final product is the metathetic diolefin 6 which two (aminomethylene)malononitrile functions.Addition of acetylenedicarboxylic esters to 2 gives -bicyclic 9, which exhibits a very facile thermal rearrangement to the diazasilacycloheptadiene 10. 1,4-Diamino-1,3-butadiene-2,3-dicarboxylic esters 12 result from the sovolysis of the N-Si bonds and exhibit a slow equilibration between different E/Z configurations.The solvolysis can be interrupted after the splitting of only one N-Si bond (13) or - in acidic medium - can be directed to the formation of the 3,4-pyrroledicarboxylic ester 14.The faster hydrolysis of the esters 9 or 10 in aqueous alkali yields a partial lactam or salts of the bis(alkylamino)butadienedicarboxylic acid (15, 16).
