162374-90-5Relevant academic research and scientific papers
Ring-Opening of (Cyclobutylmethyl)lithium and pentyl)methyl>lithium
Bailey, William F.,Punzalan, Eric R.,Della, Ernest W.,Taylor, Dennis K.
, p. 297 - 300 (1995)
The ring-opening of (cyclobutylmethyl)lithium (1) to 4-pentenyllithium (2) has been investigated in a solvent system composed of isooctane-dibutyl ether (3:2 by volume).The isomerization of 1 to 2, which is much more rapid than is cleavage of the corresponding Grignard reagent, is characterized by the following activation parameters: Ea = 14.7+/-1.2 kcal/mol, ln A = 21.6+/-2.5; ΔH(excit.) = 14.2+/-1.2 kcal/mol, ΔS(excit.) = -17.3+/-5 eu.The two-step isomerization of pentyl)methyl>lithium (5) to 4-tert-butyl-2-methylidene-4-pentenyllithium (7) via lithium (6) in pentane-diethyl ether involves a very rapid initial ring-opening of 5 to 6 (t1/2 1/2 ca. 24 min at -7.7 deg C).
