Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena.

The preparation of the vinylogue guanidinium salt <bold>10c</bold> is described. The reaction of the vinylogue orthocarbonic acid amide derivative <bold>12</bold> with CH2-acidic compounds <bold>14a–s</bold> affords the ketene aminals <bold>15a–s</bold>. At room temperature the succinimide <bold>19a</bold> is deprotonated by <bold>12</bold> to give the vinylogue salt <bold>10e</bold>. The bis-ketene aminal <bold>20</bold> is formed in the reaction of <bold>19a</bold> with <bold>12</bold> at elevated temperatures. Succinic acid esters <bold>21</bold> do not react cleanly with the orthoamide <bold>12</bold>, but mixtures of ketene aminals <bold>23</bold> and bis-ketene aminals <bold>22</bold> are formed. From succinodinitrile (<bold>24</bold>) and <bold>12</bold> the bis-ketene aminal <bold>25</bold> could be obtained, which is also accessible by the action of the salt <bold>10c</bold> with <bold>24</bold> in the presence of sodium hydride. [ABSTRACT FROM AUTHOR]