Journal of Organic Chemistry p. 1177 - 1182 (1981)
Update date:2022-08-05
Topics:
Hill, Alexander E.
Link, Daniel C.
Donndelinger Peter
(2,2-Dimethyl-4-penten-1-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 2E-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.
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Doi:10.1021/ja01290a043
(1937)Doi:10.1021/jo00320a038
(1981)Doi:10.1016/0040-4020(82)80100-2
(1982)Doi:10.1021/ja00391a024
(1981)Doi:10.1248/cpb.31.4312
(1983)Doi:10.1021/ja047983a
(2004)
