zinc(II) chloride T=100°C; 9 h; Inert atmosphere;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydride 1.) THF, 2.) THF, r. t., 7 h;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydride 1.) THF, 2.) THF, r. t., 22 h;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydride 1.) THF, 2.) THF, r. t., 16 h;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydride 1.) THF, 2.) THF, r. t., 19 h;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydride 1.) THF, 2.) THF, r. t., 6 h;

18-crown-6 ether; Pd(dppe); potassium hydride 1) THF, r.t., 10 min, 2) THF, 67 deg C, 18 h; Yield given. Multistep reaction. Yields of byproduct given;

potassium tert-butylate; Pd(dppe) multistep reaction; conditions: different reagents, different solvents, different temperatures and times; Product distributionMechanism;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '774261', constants.ctx, '0')">malonic acid dimethyl ester</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=0 - 25&deg;C;&nbsp;1&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '1736711', constants.ctx, '0')">1-iodo-4-pentyne</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=0 - 60&deg;C;&nbsp;12&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '774261', constants.ctx, '0')">malonic acid dimethyl ester</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8127929', constants.ctx, '0')">potassium iodide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=0 - 20&deg;C;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '2848511', constants.ctx, '0')">4-pentynyl tosylate</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=20 - 100&deg;C;&nbsp;<br /> &nbsp;