TY - JOUR
T1 - Geometrically directed lithiation of O‐Alkyloximes for the synthesis of linear polyethers
AU - Shatzmiller, Shimon
AU - Dolitzki, Ben‐Zion ‐Z
PY - 1991
Y1 - 1991
N2 - For synthetic purposes, the polyether‐based secondary alcohols 7 and 8 were prepared from acetone O‐methyloxime (1). This applies the (Z) effect for the geometry‐directed alkylation sequence, recovery of the keto group and reduction. In contrast to 11, α‐phenylthio‐substituted O‐alkyloxime 26 was found to be unsuitable as starting material for such synthesis. The strong effect of bivalent sulfur in the α‐position shadows the (Z) effect and permits only lithiation next to the sulfur atom.
AB - For synthetic purposes, the polyether‐based secondary alcohols 7 and 8 were prepared from acetone O‐methyloxime (1). This applies the (Z) effect for the geometry‐directed alkylation sequence, recovery of the keto group and reduction. In contrast to 11, α‐phenylthio‐substituted O‐alkyloxime 26 was found to be unsuitable as starting material for such synthesis. The strong effect of bivalent sulfur in the α‐position shadows the (Z) effect and permits only lithiation next to the sulfur atom.
KW - Ketone O‐alkyloximes, α‐phenylthio‐
KW - Lithiation
KW - Oxime ethers
KW - Polyethers
UR - http://www.scopus.com/inward/record.url?scp=84986641842&partnerID=8YFLogxK
U2 - 10.1002/jlac.199119910134
DO - 10.1002/jlac.199119910134
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AN - SCOPUS:84986641842
SN - 0170-2041
VL - 1991
SP - 189
EP - 194
JO - Liebigs Annalen der Chemie
JF - Liebigs Annalen der Chemie
IS - 3
ER -