SELECTIVE INCLUSION OF KETONE BY A SEXIPEDAL HOST.

Katherine L. Gifford Nash^a, Susan A. Bourne^a, Fumio Toda^b. a) Department of Chemistry, University of Cape Town, Rondebosch, 7700, South Africa. b) Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama 790, Japan.

Hexakis(3-hydroxy-3,3-diphenyl-2-propenyl)benzene (H) has proved to be a very versatile host including a number of small organic molecules via hydrogen bonding. Inclusion compounds of H have been found to form in various host:guest ratios, often considerably richer in guest than is usually observed for organic hosts. It includes a number of guests with carbonyl functions, for example methyl ethyl ketone (1:3), diethyl ketone (1:2) and cyclohexanone (1:5); as well as guests such as diethyl ether (1:2) and 1,4-dioxane (1:5).

However, on crystallization from 1,3-dioxolane, H selectively included a trace amount of 1,3-dioxolan-2-one from the solution. This ketone complex was characterised by single crystal diffraction, thermal analysis, nuclear magnetic resonance spectroscopy, and mass spectroscopy.