Fruns-Stilbene

A detailed study has been made of the base-catalysed deoxygenation of carbonyl compounds with diphenylphosphine oxide (52) at high temperatures. The known formation of good yields of frun -stilbene (56a) from benzaldehyde (53a) has been shown to involve the intermediate formation of cis- and mw5-stilbene epoxides, and their subsequent deoxygenation by (52). Similar deoxygenation of benzoylferrocene (53b) results in the formation of the ketones (54) and (55), as well as the hydrocarbons (56b) and (57). The rationalization given in Scheme 9 has been presented to explain these observations. ... 

A pressure bottle charged with fruns-stilbene and chromium (III) acetylacetonate as the transition metal compound, evacuated, flushed with N2, pressured with Hg, Ng-flushed toluene and triisobutylaluminum as the catalyst alkylation agent in n-heptane injected by syringe, the resulting soln. stirred 20 hrs. at room temp, and 3.7 atm. bibenzyl. Y 78%. F. e., also with the more active catalysts prepared from iron (III) and cobalt (III) acetylacetonates, s. M. F. Sloan, A. S. Matlack, and D. S. Breslow, Am. Soc. 85, 4014 (1963). 

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