TY - JOUR
T1 - Reaction of α‐lithio O‐alkyloximes with diiodomethane – a synthesis of α‐iodomethylene oxime ethers
AU - Shatzmiller, Shimon
AU - Lidor, Ramy
AU - Babar, Eliezer
PY - 1991
Y1 - 1991
N2 - Regiocontrolled deprotonation (e. g. lithiation) of acetone O‐methyloxime (1), 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine (9a) and 4,5‐dihydro‐3‐methylisoxazole (9b) is achieved within 1 minute at −65°C in hexane/THF. The lithiated compounds react very fast at low temperature (−65°C) with diidomethane to give mainly the corresponding α‐iodomethylene oxime ethers 6 and 11a, b. A radical mechanism of this reaction is discussed.
AB - Regiocontrolled deprotonation (e. g. lithiation) of acetone O‐methyloxime (1), 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine (9a) and 4,5‐dihydro‐3‐methylisoxazole (9b) is achieved within 1 minute at −65°C in hexane/THF. The lithiated compounds react very fast at low temperature (−65°C) with diidomethane to give mainly the corresponding α‐iodomethylene oxime ethers 6 and 11a, b. A radical mechanism of this reaction is discussed.
KW - 1‐Azabutadiene
KW - Iodomethylene oxime ethers
KW - Oxime ethers
UR - http://www.scopus.com/inward/record.url?scp=84986680751&partnerID=8YFLogxK
U2 - 10.1002/jlac.199119910166
DO - 10.1002/jlac.199119910166
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AN - SCOPUS:84986680751
SN - 0170-2041
VL - 1991
SP - 381
EP - 383
JO - Liebigs Annalen der Chemie
JF - Liebigs Annalen der Chemie
IS - 4
ER -