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By Richard F. Heck

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Extra resources for Organotransition Metal Chemistry a Mechanistic Approach

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6. Reactions of Metal Complexes with Diazo Compounds Most hydrido transition metal compounds will react with diazo compounds to form nitrogen and the alkyl metal derivative. For example (81), CpMo(CO)3H + CH 2 N 2 -► CpMo(CO)3CH3 + N2 This reaction may also be considered a 1:1 addition of the hydride to a carbene. Similar reactions occur with halotransition metal complexes producing halomethyl derivatives. NC + N 2 CHCN + N2 (Ref. 82) B. Methods of Preparation of Carbon-Transition Metal Bonds 41 7.

One of the most thoroughly studied homogeneous hydrogenation catalysts is hydridocarbonyl(tristriphenylphosphine)rhodium(I) which has been investigated by Wilkinson and co-workers (114). This catalyst readily causes hydrogen reduction of terminal olefins to hydrocarbons at 25°C and atmospheric pressure, but internal olefins are very much less reactive. 69r as a double quartet with 1:3:3:1 area ratios. The three triphenylphosphine groups are apparently all equivalent causing splitting of the hydride resonance into a quartet (/ P _ H = 1 4 Hz) and the 103 Rh causing a doubling of the quartet (/Rh—H = 1 Hz).

The true L n M—H \ L»-iM—H + C=C / 7 II II H L + L»-iM—H \ / / I \ " L»-iM—H ^ = ± ii I I U-iM H L ; = ± I' I I LnM H II —c—c— Ln-iM , , M» —c—c— II L„-iM /\ H H H II ► Ln-iM—H + —C—C— I I H H situation may be even more complicated than these equations indicate since both the olefin-metal hydride π complex and the dihydridoalkyl metal complex intermediates generally may exist in more than one isomeric form. Only isomers which have the reacting hydrogen and the carbon groups eis to each other can directly undergo the necessary reactions.

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