Water → cis-Stilbene

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To the solution of one equivalent of TiCl4 (1.1 ml, 10 mmol) and 0.5 equivalent of diphenylacetylene (0.89g, 5 mmol) in THF (40 ml) at −78° C. 2 equivalents of n-butyllithium (12.5 ml, 20 mmol, 1.6M solution in hexane) was slowly added and the resulting red-brown reaction mixture stirred at −78° C. for 1 h. The reaction mixture was then allowed to warm up to room temperature over 0.5 h followed by hydrolysis with 20 ml of H2O. Extraction of the organic products was accomplished with ether anhydrous ether. cis-Stilbene (91%) and bibenzyl (0.4%) were obtained as the products.

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