14.11 Alkane Synthesis Using Organocopper Reagents
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1 14.11 Alkane Synthesis Using Organocopper Reagents
2 Lithium Dialkylcuprates Lithium dialkylcuprates are useful synthetic reagents. They are prepared from alkyllithiums and a copper(i) halide. 2RLi + CuX R 2 CuLi + LiX [customary solvents are diethyl ether and tetrahydrofuran (THF)]
3 How? the alkyllithium first reacts with the copper(i) halide R Li R Li + Cu I Cu I
4 How? the alkyllithium first reacts with the copper(i) halide R Li R Li + Cu I then a second molecule of the alkyllithium reacts with the alkylcopper species formed in the first step R Cu R Li R Cu I R Cu Li +
5 Lithium diorganocuprates are used to form C C C C bonds R 2 CuLi + R'X R R' + RCu + LiX Ar 2 CuLi + R'X Ar R' + ArCu + LiX
6 Example: Lithium dimethylcuprate (CH 3 ) 2 CuLi + CH 3 (CH 2 ) 8 CH 2 I diethyl ether CH 3 (CH 2 ) 8 CH 2 CH 3 (90%) primary alkyl halides work best (secondary and tertiary alkyl halides undergo elimination)
7 Example: Lithium diphenylcuprate (C 6 H 5 ) 2 CuLi + CH 3 (CH 2 ) 6 CH 2 I diethyl ether CH 3 (CH 2 ) 6 CH 2 C 6 H 5 (99%)
8 Vinylic halides can be used (CH 3 CH 2 CH 2 CH 2 ) 2 CuLi + Br diethyl ether CH 2 CH 2 CH 2 CH 3 (80%)
9 Aryl halides can be used (CH 3 CH 2 CH 2 CH 2 ) 2 CuLi + I diethyl ether CH 2 CH 2 CH 2 CH 3 (75%)
10 14.12 An Organozinc Reagent for Cyclopropane Synthesis
11 Iodomethylzinc iodide formed by reaction of diiodomethane with zinc that has been coated with copper (called zinc-copper copper couple) CH 2 I 2 Cu + Zn ICH 2 ZnI reacts with alkenes to form cyclopropanes reaction with alkenes is called the Simmons-Smith Smith reaction
12 Example H 2 C C CH 2 CH 3 CH 3 CH 2 I 2, Zn/Cu diethyl ether CH 2 CH 3 CH 3 (79%)
13 Stereospecific syn-addition CH 3 CH 2 CH 2 CH 3 C C H CH 2 I 2, Zn/Cu H diethyl ether CH 3 CH 2 H CH 2 CH 3 H
14 Stereospecific syn-addition CH 3 CH 2 H C C H CH 2 I 2, Zn/Cu CH 2 CH 3 diethyl ether CH 3 CH 2 H H CH 2 CH 3
15 14.13 Carbenes and Carbenoids
16 Carbene name to give to species that contains a divalent carbon (carbon with two bonds and six electrons) Br C Br dibromocarbene Carbenes are very reactive; normally cannot be isolated and stored. Are intermediates in certain reactions.
17 Generation of Dibromocarbene Br Br C Br H + OC(CH 3 ) 3 Br Br C Br + H OC(CH 3 ) 3
18 Generation of Dibromocarbene Br C Br + Br Br Br C Br
19 Carbenes react with alkenes to give cyclopropanes + CHBr 3 KOC(CH 3 ) 3 (CH 3 ) 3 COH Br Br CBr 2 is an intermediate stereospecific syn addition (75%)
20 14.14 Transition-Metal Organic Compounds
21 Introduction Many organometallic compounds derived from transition metals have useful properties. Typical transition metals are iron, nickel, chromium, platinum, and rhodium.
22 18-Electron Rule The number of ligands attached to a metal will be such that the sum of the electrons brought by the ligands plus the valence electrons of the metal equals 18. When the electron-count count is less than 18, metal is said to be coordinatively unsaturated and can take on additional ligands. 18-Electron rule is to transition metals as the octet rule is to second-row elements.
23 Example OC CO Ni CO CO Nickel carbonyl Ni has the electron configuration [Ar]4s 2 3d 8 Ni has 10 valence electrons Each CO uses 2 electrons to bond to Ni 4 CO contribute 8 valence electrons = 18
24 Example OC Cr CO (Benzene)tricarbonylchromium CO Cr has the electron configuration [Ar]4s 2 3d 4 Cr has 6 valence electrons Each CO uses 2 electrons to bond to Cr 3 CO contribute 6 valence electrons benzene uses its 6 π electrons to bind to Cr.
25 Example Fe Ferrocene Fe 2+ has the electron configuration [Ar]3d 6 Each cyclopentadienide anion contributes 6 π electrons Total = 18 Organometallic compounds with cyclopentadienide ligands are called metallocenes.
26 14.15 Ziegler-Natta Catalysis of Alkene Polymerization The catalysts used in coordination polymerization are transition-metal organic compounds.
27 Ethylene oligomerization n H 2 C CH 2 Al(CH 2 CH 3 ) 3 CH 3 CH 2 (CH 2 CH 2 ) n-2 CH CH 2 Triethylaluminum catalyzes the formation of alkenes from ethylene. These compounds are called ethylene oligomers and the process is called oligomerization.
28 Karl Ziegler (1950) n H 2 C CH 2 Al(CH 2 CH 3 ) 3 CH 3 CH 2 (CH 2 CH 2 ) n-2 CH CH 2 Ziegler found that oligomerization was affected differently by different transition metals. Some gave oligomers with carbons, others gave polyethylene.
29 Karl Ziegler (1950) n H 2 C CH 2 Al(CH 2 CH 3 ) 3 CH 3 CH 2 (CH 2 CH 2 ) n-2 CH CH 2 The ethylene oligomers formed under Ziegler's conditions are called linear α-olefins and have become important industrial chemicals.
30 Karl Ziegler (1950) n H 2 C CH 2 Al(CH 2 CH 3 ) 3 CH 3 CH 2 (CH 2 CH 2 ) n-2 CH CH 2 The polyethylene formed under Ziegler's conditions is called high-density polyethylene and has, in many ways, more desirable properties than the polyethylene formed by free-radical radical polymerization.
31 Giulio Natta n H 2 C CHCH 3 Al(CH 2 CH 3 ) 3 polypropylene Natta found that polymerization of propene under Ziegler's conditions gave mainly isotactic polypropylene. This discovery made it possible to produce polypropylene having useful properties.
32 Ziegler-Natta Catalysts A typical Ziegler-Natta catalyst is a combination of TiCl 4 and (CH 3 CH 2 ) 2 AlCl, or TiCl 3 and (CH 3 CH 2 ) 3 Al. Many Ziegler-Natta catalyst combinations include a metallocene.
33 Mechanism of Coordination Polymerization Al(CH 2 CH 3 ) 3 + TiCl 4 ClAl(CH 2 CH 3 ) 2 + CH 3 CH 2 TiCl 3
34 Mechanism of Coordination Polymerization Al(CH 2 CH 3 ) 3 + TiCl 4 ClAl(CH 2 CH 3 ) 2 + CH 3 CH 2 TiCl 3 CH 3 CH 2 TiCl 3 + H 2 C CH 2 CH 3 CH 2 TiCl 3 H 2 C CH 2
35 Mechanism of Coordination Polymerization CH 3 CH 2 TiCl 3 H 2 C CH 2
36 Mechanism of Coordination Polymerization TiCl 3 CH 3 CH 2 CH 2 CH 2 CH 3 CH 2 TiCl 3 H 2 C CH 2
37 Mechanism of Coordination Polymerization TiCl 3 CH 3 CH 2 CH 2 CH 2 H 2 C CH 2 H 2 C CH 2 TiCl 3 CH 3 CH 2 CH 2 CH 2
38 Mechanism of Coordination Polymerization CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 TiCl 3 H 2 C CH 2 TiCl 3 CH 3 CH 2 CH 2 CH 2
39 Mechanism of Coordination Polymerization CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 TiCl 3 H 2 C CH 2 etc.
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