Carbocycles ring expansion

C. D. Gutsche and D. Redmore, Carbocyclic Ring Expansion Reactions, Academic Press, New York, 1968, pp. 163-170. 

Gutsche, C.D. Redmore, D. "Carbocyclic Ring Expansion Reactions" Academic Press New York, N.Y., 1968. 

In 1968, an excellent review on Carbocyclic Ring Expansion Reactions was published [1], Most of the reaction discussed there are one carbon atom insertions. Our review will be limited to discussions of newer methods. Well known reactions are summarized only by giving the principal reaction and leading additional references. The principal reactions for one carbon insertion are summarized in Scheme II/l. 

Since Reppe s discovery of the cyclotrimerization of acetylene to benzene in the presence of nickel carbonyl-phosphine complexes, the use of nickel catalysts in many organic transformations has become popular. Transition metal complex catalysis provides many elegant entries to carbon-carbon bond-forming reactions in organic synthesis. One notable example is carbocyclic ring expansion mediated by nickel(O) complexes. ... 

Scheme 5 First example of carbocyclic ring expansion using diazomethane ...

Gutsche CD, Redmore D (1968) In Hart H, Karabatsos GJ (eds) Carbocyclic ring expansion reactions. Academic, New York, pp 81-98... 

Finally, alkyltins can participate in radical chemistry, especially when the /3-elimination is thermodynamicaly favored, leading, for instance, to carbocyclic ring expansions [313], In a similar way, radical reactions involving a 1,3-stannyl shift could afford 5-exo cyclizations [314]. 

---