Reactivity of a Linear 2-Germapropadiene with Acids, Ketones, and Amines

Abstract

The reactivity of an isolable 2-germapropadiene with acids, ketones, and amines was investigated. The reactions of 2-germapropagiene 1 with hydrogen chloride and acetic acid afforded the corresponding dichlorogermane (2) and diacetoxygermane (3), respectively, indicating that the central germanium atom of 1 is electrophilic. The reaction of 1 with benzaldehyde proceeds via a formal [2+2] cycloaddition to afford the corresponding spiro compound (4). Moreover, 1 reacts smoothly with acetone to furnish germane 5, which contains a six-membered ring involving two acetone molecules. Furthermore, 1 undergoes N-H bond insertion with methylamine or aniline to afford diamino germanes 7 and 8, respectively. The reaction of 1 with urea selectively afforded the corresponding N-H-insertion product (8).

Keywords: Heavy allenes; Organogermanium compounds; Single-crystal X-ray diffraction analysis.