12.5 Organometallic Compounds
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1 12.5 rganometallic Compounds
2 Compounds that contain carbon-metal bond are called organometallic compounds. C M C δ δ + M C M Primarily ionic Primarily covalent (M = Na + or K + )(M = Mg or Li) (M = Pb, Sn, Hg, or Tl) The reactivity of organometallic compounds increases with the percent ionic character of the carbon-metal bond. RLi and RMgX are of great importance in organic synthesis.
3 12.6 Preparation of rganolithium and rganomagnesium Compounds
4 12.6A rganolithium Compounds rganolithium compounds are often prepared by th reduction of organic halides with lithium metal. Et 2 R X + 2 Li RLi + LiX (or Ar X ) (or ArLi) Reactivity: RI > RBr > RCl CH 2 CH 2 CH 2 Br + 2 Li Butyl bromide Et 2 10 C CH 2 CH 2 CH 2 Li + LiBr Butyllithium (80 ~ 90%)
5 12.6B Grignard Reagents Grignard reagents are usually prepared by the reaction of an organic halide and magnesium metal in an ether solvent. R Ar X X Et 2 + Mg RMgX + Mg Et Grignard 2 or THF reagents ArMgX I + Mg Et 2 MgI 35 C Methylmagnesium iodide C 6 H 5 Cl + Mg THF C 6 H 5 MgCl Phenylmagnesium chloride
6 12.7 Reactions of rganolithium and rganomagnesium Compounds
7 12.7A Reactions with Compounds Containing Acidic Hydrogen Atoms Grignard reagents and organolithium compounds are very strong bases. They react with any compounds that has a hydrogen attached to an electronegative atom such as oxygen, nitrogen, or sulfur. RMgX HH R'H RH RH + + H + Mg 2+ + X R' + Mg 2+ + X R'C CH RH + R'C δ δ + C MgX RLi + R'C CH R'C C Li δ δ + RH +
8 12.7B Reactions of Grignard Reagents with xiranes (Epoxides) RMgX + H 2 C CH 2 RCH 2 CH 2 MgX H+ RCH 2 CH 2 H C 6 H 5 MgBr + H 2 C CH 2 (1) Et 2 (2)H 2 /H + C 6 H 5 CH 2 CH 2 H C 6 H 5 MgBr + H 2 C CH (1) Et 2 (2)H 2 /H + C 6H 5 CH 2 CH H
9 12.7C Reactions of Grignard Reagents with Carbonyl Compounds RMgX + C (1) Et 2 (2)H 2 /H + R C H + MgX 2 Mechanism δ δ + R MgX+ C R C MgX R C MgX + H H R C H + H + MgX H H
10 12.8 Alcohols from Grignard Reagents
11 Grignard Reagents React with Formaldehyde to Give a Primary Alcohol RMgX + CH 2 (1) Et 2 (2)H 2 /H + R CH 2 H 1 Alcohol Grignard Reagents React with All ther Aldehydes to Give a Secondary Alcohols RMgX + R'CH (1) Et 2 (2)H 2 /H + R R' CHH 2 Alcohol
12 Grignard Reagents React with Ketones to Give a Tertiary Alcohols RMgX + R' R" C R' (1) Et 2 (2)H 2 /H + R C H R" 3 Alcohol Esters React with Two Equivalents of a Grignard Reagent to Form Tertiary Alcohols RMgX R' C R R' R' + C R C MgX R" R" RMgX R' R C MgX NH 4Cl H R 2 R R' C R H
13 12.8A Planning a Grignard Synthesis CH 2 C CH 2 + C 6 H 5 MgBr C 6 H 5 C 6 H 5 C R + 2 CH 2 MgBr CH 2 C CH 2 H CH 2 C C 6 H 5 + CH 2 MgBr
14 12.8B Restrictions on the Use of Grignard Reagents The Grignard reagent is a very powerful base. Thus, it is not possible to prepare a Grignard reagent from an organic group that contains an acidic hydrogen. H NH 2 NHR C 2 H S 3 H SH C CH We cannot prepare a Grignard reagent from any organic halide that contains a carbonyl, epoxy, nitro, or cyano group. CR CR CNH 2 N 2 C N
15 12.8C The Use of Lithium Reagents δ δ + R Li + C R C Li H 2 /H + R C H H (1) Et 2 CH 2 CHLi + CH CH CH CH (2)H 2 2 /H + C C 2 Et (1) Li (2) H 3 + C C H
16 12.8D The Use of Sodium Alkynides C CH 3 C δ Na δ + C C C CH C Na 3 H 2 /H + C C C H
17 12.9 Lithium Dialkylcuprates: The Corey-Posner, Whitesides-House Synthesis
18 R X + 2 Li Et 2 RLi + LiX 2 RLi + CuI R 2 CuLi + LiI Alkyllithium Lithium dialkylcuprate R 2 CuLi + R" X Lithium Alkyl halide dialkylcuprate R" = 1 or 2 alkyl halide R R" RCu + LiX + Alkane R X RLi R 2 CuLi R" X R R" Corey-Posner, Whitesides-House synthesis
19 ( ) 2 CuLi + (CH 2 ) 6 CH 2 I Et 2 CH3 (CH 2 ) 6 CH 2 (90%) (C 6 H 5 ) 2 CuLi + (CH 2 ) 6 CH 2 I Et 2 CH3 (CH 2 ) 6 CH 2 C 6 H 5 (99%) ( CH 2 CH 2 CH 2 ) 2 CuLi + Br Et 2 CH 2 CH 2 CH 2 (80%) ( CH 2 CH 2 CH 2 ) 2 CuLi + I Et 2 CH 2 CH 2 CH 2 (75%)
20 12.10 Protecting Groups
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