Friday, 19 February 2016

Organic Chemistry: C-C Bond Forming Reactions, Part II


4.   Kolbe’s Electrolysis

This is an electrolytic decarboxylation of carboxylic acids. The mechanism involves the formation and coupling of alkyl radicals to form a C-C bond.



5.   Organometallic Reactions

Organometallic compounds possess a nucleophilic carbon atom which reacts with variety of compounds having electrophilic carbons to form C-C bonds. Some of the most common organometallic compounds used are Grignard reagent, organo lithium, organosodium, organozinc, and organocopper reagents.

a.      Reaction with Carbonyl Compounds


b.      Reaction with a,b-unsaturated carbonyl compounds

Different organometallic compounds react differently with unsaturated carbonyl compounds. The nucleophilic carbon may attack the carbonyl carbon (direct addition) or the b-carbon (conjugate addition or Michael addition).

c.       Reaction with Epoxide

Organometallic compounds opens the epoxide ring.
6.   Claisen Condensation

The self-condensation of esters is known as Claisen condensation. A common example is the acetoacetic ester synthesis.

7.   Cross Coupling Reactions

Some important coupling reactions are Suzuki coupling, Stille coupling, Hiyama coupling, Nigishi coupling, Heck reaction, and Kumada couplings. All of these reactions involve the formation of a single bond between carbon atoms.

The mechanism of these cross coupling reactions involve some common steps, viz. oxidative addition, transmetallation, and reductive elimination.


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