Abstract
Bis(triphenylphosphine)nickel(II) chloride reacts with E,E,-1,4-dilithio-1,2,3,4-tetraphenylbutadiene to yield a solution of a 2,3,4,5-tetraphenylnickelole complex. This compound reacts promptly with CO to yield tetracyclone, with dimethyl acetylenedicarboxylate to form dimethyl tetraphenylphthalate and catalytically with diphenylacetylene to form hexaphenylbenzene. A similar treatment of (1,2-bis(diphenylphosphino)ethane)nickel(II) chloride with the lithium reagent led to the isolation of (1,2-bis(diphenylphosphino)ethane)bis(2,3,4,5-tetraphenylnickelole), which likewise reacts with dimethyl acetylenedicarboxylate to yield dimethyl tetraphenylphthalate. These results support the interpretation that nickeloles are reactive intermediates in the cyclotrimerization of alkynes by nickel(0) catalysts.
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