STABLE GERMA-IMINES - SYNTHESIS AND REACTIVITY OF ORTHOSUBSTITUTED ANILINODIMESITYLGERMA-IMINES

The orthosubstituted anilinodimesitylgerma-imines Mes(2)Ge=NAA (1) and Mes(2)Ge=NAE (2) where NAA is N-(dimethylanthranilamide) and NAE is N-(methylanthranilate) have been prepared by dehydrohalogenation of the corresponding halogenogermylamines. They are rare examples of thermally stable and monomeric germa-imines, probably stabilized by intramolecular C=O --> Ge coordination. They readily undergo addition reactions with water, ethanol, germanols, phenylacetylene and chloroform to form adducts in which the protonic H is bonded to nitrogen. They also add to 3,5-ditert-butylorthoquinone, forming thermally unstable (2 + 4) and (2 + 2) adducts which rearrange to the expected digermadioxolane and dimesitylgermoxane respectively. By 1-3 cycloaddition, N-tert-butyl-phenylnitrone adds to germa-imines 1 and 2, yielding the first stable 1-oxa-2,4-diaza-5-germolanes.