(2,2-Dimethyl-4-penten-l-yl)magnesium bromide (1) is in equilibrium with its cyclic isomer, [(3,3-dimethylcyclobutyl) methyl]magnesium bromide (2). The equilibrium constant for this cyclization has a value of 2 X 10-3. The gem-dimethyl substitution leads to an increase of a factor of about 22 in the equilibrium constant and also retards the rate of cleavage of 2. The sources of the gem-dimethyl effect in this system are discussed.
|Number of pages||6|
|Journal||Journal of Organic Chemistry|
|State||Published - Mar 1981|