Chapter 1 Carbon—carbon bond formation utilizing tin and lead organometallics (pages 1–97): V. G. Kumar Das and Chit?Kay Chu
Chapter 2 Carbon—carbon bond formation utilizing organometallic compounds of zinc, cadmium, and mercury (pages 99–141): Leone Miginiac
Chapter 3a half 1. ?3?Allylnickel complexes (pages 143–162): G. Paolo Chiusoli and Giuseppe Salerno
Chapter 3b half 2. ?3?Allylpalladium complexes (pages 163–199): Jiro Tsuji
Chapter 3c half three. different ?3?allyl transition steel complexes (pages 201–204): Fumie Sato
Chapter four Olefin oligomerization (pages 205–257): Olav?T. Onsager and Jon Eigill Johansen
Chapter five Alkyne oligomerization (pages 259–294): Mark J. Winter
Chapter 6 Transition steel carbonyls in natural synthesis (pages 295–333): Julian A. Davies and Randy J. Shaver
Chapter 7 Olefin and alcohol carbonylation (pages 335–359): Gordon okay. Anderson and Julian A. Davies
Chapter eight Olefin hydroformylation (pages 361–389): Julian A. Davies
Chapter nine The Fischer—Tropsch synthesis (pages 391–434): G. Henrici?Olive and S. Olive
Chapter 10 Olefin carbonylation (pages 435–445): Donald M. Fenton and Eric L. Moorehead
Read or Download The Metal - Carbon Bond: Volume 3 (1985) PDF
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Additional resources for The Metal - Carbon Bond: Volume 3 (1985)
A zwitterionic intermediate has been inferred for this reaction (Scheme 20). 1. Carbon -carbon (NC),C=C(CN), f bond formation 51 Ph3SnCH2CH=CH2 SCHEME 20 The thermal Diels- Alder reactions of mono- and bis-trimet hylstannylcyclopentadienes with hexafluorobut-2-yne yield the appropriate bicyclic adducts in moderate yields’ (equation f 57). The bis-substituted compound, however, isomerizes on forming the adduct. The use of the trimethylstannylisoprene (69)as a five-carbon isoprcne synthon has been *’ f CF3C=CCF3 RT -----+ lIO-lZO ( 157) h M Re&cF3 cF3 R = H, SnMe3j 52-53% V.
G. Kumar Das and Chit-Kay Chu For the case of the stannol reagent 50,the expected bicyclic adduct was observed with tetracyanoethylene, but not with benzyne13* (equatiom 108 2nd 109). O n treatment with bromine 50 yields the acyclic product 51, the oxidative pyrolysis’39 of which in benzene has been shown to procezd through the intermediate tetraphenylbutadiene, trapped as the NiBr, complex 52 (equation 110). 50 0% Ph-C- C- I C-Ph 11 Ph-C I BII Me2SnBr Ph 100-150 OCP5 PhH , 0, [:hnrh ] 1 NlBr, (51) A retro-Diels- Alder reaction has been reported by Considine and coworkers’40 in the thermolysis of both exo- and endo-norborn-2-en-5-yltrimethyltin (equation 1 1 1).
OH F2 I R R' ( 1 37)'64 SnF2/drnf 2. RCHO - OH RCHO R' (138)'64 1. Carbon-carbon bond formation (56) 43 ( I 39)165 in aldol additions have been made'65-168. In general, crotyltins appear to be less reactive than allyltins towards aldehydes and ketones'". H a l ~ g e n ' ~or ~ *additional '~~ ally1 moieties'6S on tin enhance the reactivity. Thus, compared with tributylallyltin, both tetraallyltin and dibutyl(croty1)tin chloride (57) react exothermically with aldehydes at room temperature and with non-activated ketones at moderate temperatures.