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Metalation Reactions XIII. Effect of the Metalating Agent on the Metalation of Acetylenes
Author(s) -
Becker J. Y.,
Brenner S.,
Klein J.
Publication year - 1972
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197200083
Subject(s) - chemistry , metalation , protonation , lithium (medication) , propyne , alkylation , medicinal chemistry , silylation , organic chemistry , catalysis , ion , medicine , endocrinology
Methyl‐lithium gave with 1‐phenyl‐1‐propyne and 1‐phenyl‐1‐butyne preferentially the products of monometalation although dimetalation of these compounds is faster than monometalation when butyl‐lithium is used. The product of protonation of dilithiophenylbutyne depends on the condition of the reaction. In the presence of starting material, 4‐phenylbut‐2‐yne and in its absence, 1‐phenylbuta‐1,2‐diene is obtained. Alkylation, silylation and protonation of the lithium derivatives was studied.