Cheong PH1, Morganelli P, Luzung MR, Houk KN, Toste FD.
J Am Chem Soc. 2008 Apr 2;130(13):4517-26. doi: 10.1021/ja711058f. Epub 2008 Mar 8.Tris(triphenylphosphinegold) oxonium tetrafluoroborate, [(Ph3PAu)3O]BF4, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidence shows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond to a cationic phosphinegold(I)-complexed phosphinegold(I) acetylide, followed by a 1,5-hydrogen shift.