The Organic Chemistry of Nickel. Organic Synthesis by P.W. Jolly (Auth.)

By P.W. Jolly (Auth.)

The natural Chemistry of Nickel

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The Organic Chemistry of Nickel. Organic Synthesis

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B Ni - ^ Ci Ξ c Ni-*CiS Ni-H : : ; H2C = C H C H 3 Ni—C ! i ; H2C===CHCri3 Ni H : : . CH3CH=CH2 Ni C Ni-+C2E= : : . CH3CH:^Cri2 Ni -► C 2 s 25 ///. Oligomerization and Co-oligomerization following insertion of propylene into the Ni-C 2 H 5 bond occurs preferentially in an Ni -> Cx sense, as predicted from Table 1-6. R3P- R3R: Hr I CH3 HCCH 3 / CH2 I CH3 I - CH2 '. CCH2CH3 CH3 Partial support for the mechanism outlined above has been obtained by studying model complexes. The formation of a nickel-alkyl by the addition of a nickel-hydride to an olefin has been observed in the reactions of the πallylnickel hydride 19 with ethylene (143; see Volume I, p.

Oligomerization of Olefins CH2 I CH3 principally a Ni-n-propyl species (Ni -+ d ) that rearranges to the thermo· dynamically more stable Ni-isopropyl species (Ni -► C2) (141). J2H2 CH3 The same choice exists in the second step and leads to the situation shown on p. 23. It is apparent from this scheme that the distribution of the products enables an estimate to be made of the direction of addition (Ni -> Cx or Ni -> C2). For thefirststep this is given by 70 N i - * C i 7o Ni -> C2 7o (4-methyl-l-pcntene + 4-methyl-2-pentene + 2,3-dimethyl-l-butène) % (2-methyl-l-pentene + 1-hexene + 2-hexene) and for the second step by 70 N i - > C i 7o (4-methyl-l-pentene + 4-methyl-2-pentene + 1-hexene + 2-hexene) 70 Ni -^ C 2 7o (2,3-dimethyl-l-butene + 2-methyl-l-pentene) CH2—ν^ΗΟΗ2ν-Ή2^Η2ν^Η; CH3 I -NiH > Hexene Ni—CHCHaCHaCHaCHa Ni—CH2CH2CH3 Ni-* d CJHa 1CHCH3 Ni -* C 2 CH3CH—CHCH2CH2CH3 CH3 CH3 Ni—CH2CHCH2CH2CH3 Ni-* d Ni—H + -NiH —*■ C H 2 — C C H 2 C H 2 C H 3 CH3 CH2=::CHCH3 I CH3 I 4\ CH3 I Ni—CHCH3 Ni-*Ca I Ni—CHCH2CHCH3 > Methylpentene CH2—CHCH2CHCH3 OH3 -NiH CH3 Ni-*Ca I CHa : CHCH3 CH3CH=CHCHCH3 CH3 CH3 Ni—CH2CH—CHCH 3 Ni-* d H3C -NiH CH3 -► CH2=C—CHCH3 2,3-Dimethylbutene 24 /.

147, P167 160 28, 167, 176, 331, P48 168-170, 172; see also 194 159 96, 163, 164, 175, 330 186, P98 148-151, 153, 327 144-147, 153-155, P164, P167 171, P170-P172 149, 152, 340 PI 66 157, 159, P173 161 162 161 P244 168-170,172,186; see also 194 328 183 173, P181 182 184 185 184 191 192, 193; see also 179 181 54 /. Oligomerization of Olefins variety of active catalysts based on nickel have been reported. The reactions of methyl methacrylate and styrene have been most thoroughly investigated, and evidence for the formation of free radicals has been obtained from reactions catalyzed by nickel tetracarbonyl (150, 327) and tetrakistriphenylphosphite nickel (144-147, 153-155, 189, 336) in carbon tetrachloride, as well as by bis(cyclooctadiene)nickel-RC02H (160).

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