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Ethoxycarbonyl-triphenylphosphonium bromide reacts with orthoamides of alkynecarboxylic acids  14  to give vinylogous guanidinium bromides, which were transformed to the corresponding tetraphenylborates. In contrast, from CH 2 -acidic phosphonicesters and orthoamides  14  phosphorylated 1,1-diamino-butadienes can be obtained. Two of these products rearrange to 5-dimethylamino-4-diet-hylphosphono-2,4-hexadienic acid amides upon heating. Reaction of phenylsulfonylated carboxylic acids and alkylketones with orthoamides  14  proceeds under condensation affording 4-phenylsulfonyl-1,1-diamino-1,3-butadienes. Accordingly, the condensation reactions between the orthoamides  14  and isocyanoacetic acid ester deliver 2-isocyano-5,5-bis(dimethylamino)-2,4-pentadienic acid esters. In one of these reactions 5,6-diamino-pyridine-2-carboxylic acid ester is obtained as a by-product. Some of the ketene aminals exist as equilibrium mixtures of stereoisomers, which is a consequence of  s -cis and  s -trans isomerism of the butadiene unit.

zeitschrift für naturforschung b

Orthoamide und Iminiumsalze, CVII a . 4-Sulfonylierte- und 4-phosphorylierte sowie 4-isocyansubstituierte-1,1-Bis(dimethylamino)-1,3-butadiene aus Sulfonen, (Alkyl)phosphonsäureestern sowie Isocyanessigsäureester und Orthoamid-Derivaten von Alkincarbonsäuren