Journal of Organic Chemistry p. 4933 - 4938 (1991)
Update date:2022-08-29
Topics:
Singer, Robert, D.
Hutzinger, Michael W.
Oehlschlager, Allan C.
The stannylcupration of terminal alkynes 4a,b with cuprates 1-3 proceeds rapidly and reversibly above -35 deg C to afford stannylcuprate intermediates 5a,b and 6a,b.These intermediates have been characterized by 2H and 13C NMR labelling experiments.Corroborating evidence for this reversible addition comes from further chemical tests and cross-over experiments that show the thermodynamic favorability of the adducts.Further comparative study of reaction products and byproducts shows 2 to be the stannylcuprate of choice for the preparation of vinylstannates from terminal alkynes.
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