1986
DOI: 10.1039/c39860000312
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Evidence for the radical pair mechanism in ‘insertion’ reactions of transition metal hydrides with conjugated dienes

Abstract: The compounds cpFe(C0)2H and HMn(C0)5 (cp = cyclopentadienyl) react with 1,3-dienes to give the 2-enylmetal products of 1,4-addition of the metal hydrides to the dienes; CIDNP studies indicate that the process involves a radical pair mechanism.

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Cited by 10 publications
(7 citation statements)
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“…In 1977, Sweany and Halpern reported strong evidence for H • transfer in the hydrogenation of α-methylstyrene by HMn(CO) 5 (Scheme ); they observed chemically induced dynamic nuclear polarization (CIDNP) and an inverse isotope effect for HMn(CO) 5 /DMn(CO) 5 . Since then, there have been numerous reports of hydrogenations that occur through H • transfer. ,
1
…”
Section: Introductionmentioning
confidence: 99%
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“…In 1977, Sweany and Halpern reported strong evidence for H • transfer in the hydrogenation of α-methylstyrene by HMn(CO) 5 (Scheme ); they observed chemically induced dynamic nuclear polarization (CIDNP) and an inverse isotope effect for HMn(CO) 5 /DMn(CO) 5 . Since then, there have been numerous reports of hydrogenations that occur through H • transfer. ,
1
…”
Section: Introductionmentioning
confidence: 99%
“…Hydroformylation reactions may also involve H • transfer. Evidence for such a step in the hydroformylation of styrene by HCo(CO) 4 is offered by an inverse H/D kinetic isotope effect ( k (HCo(CO) 4 )/ k (DCo(CO) 4 )) and by the absence of an inverse CO dependence in the rate law. ,4c …”
Section: Introductionmentioning
confidence: 99%
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“…1,2 Early reports employed stoichiometric amounts of metal hydrides and activated alkenes. [3][4][5][6][7][8][9][10][11][12][13] Recently a range of exceptionally useful alkene hydrofunctionalization reactions have been recorded by Mukaiyama, Carreira, Boger, Baran, and others using cobalt-, manganese-, and iron-based catalysts (Scheme 1a). Reports from our laboratory and Shenvi and co-workers detail methods for the reduction of alkenyl halides 43,44 and unactivated alkenes 44 by hydrogen atom transfer.…”
mentioning
confidence: 99%
“…A magnetic field effect on the ratio of the two products would be anticipated. A variety of other organometallic reactions which have been discussed in the recent literature [107][108][109][111][112][113] have similar mechanisms involving radical pairs.…”
Section: The Mechanistic Role Of Outer Sphere Complexesmentioning
confidence: 99%