M. Waters, M. Bos, W. Wulff
Jun 25, 1999
Citations
0
Influential Citations
37
Citations
Journal
Journal of the American Chemical Society
Abstract
The regioselectivity of the formation of three different products from the reaction of 1-phenylpropyne with (methoxy)(2-methoxyl-1-phenyl)methylene pentacarbonyl chromium 12 was examined in detail. The phenol product is formed with a substantial regioselectivity which is temperature-dependent, but the indene products (obtained as two compounds: indene and indenone) are formed as a nearly equal mixture of regioisomers. The proportion of indene and phenol products is dependent on the concentration with greater amounts of phenol products being formed at higher concentrations. The total regioselectivity of all of the products is also a function of the concentration. This result could be due either to an equilibration of the η1,η3-vinyl carbene intermediates in this reaction or to a change in mechanisms in the formation of the η1,η3-vinyl carbene intermediates from one involving a dissociative incorporation of the alkyne to one involving an associative incorporation of the alkyne. Kinetic studies reveal that ...