TY - JOUR
T1 - Reactions of lithium salts of O‐alkyl oximes with halogens
T2 - A highly stereoselective oxidative coupling of 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine
AU - Shatzmiller, Shimon
AU - Lidor, Ramy
AU - Bahar, Eliezer
AU - Goldberg, Israel
PY - 1991
Y1 - 1991
N2 - Lithiation of 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine (4) in an unpolar solvent system (hexane/THF) at −65°C followed by reaction with Cl2,Br2, or I2 affords cleanly and stereoselectively 6 (RS,RS) of which an X‐ray structure analysis is described. In contrast, attempts to couple the halogenated 1,2‐oxazine derivative 5c have given, under various reaction conditions, equal amouts of 6 and 8 (meso). A mechanism of this reaction is discussed.
AB - Lithiation of 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine (4) in an unpolar solvent system (hexane/THF) at −65°C followed by reaction with Cl2,Br2, or I2 affords cleanly and stereoselectively 6 (RS,RS) of which an X‐ray structure analysis is described. In contrast, attempts to couple the halogenated 1,2‐oxazine derivative 5c have given, under various reaction conditions, equal amouts of 6 and 8 (meso). A mechanism of this reaction is discussed.
KW - 4H‐1,2‐Oxazines
KW - Coupling, oxidative
KW - Oxime ethers
UR - http://www.scopus.com/inward/record.url?scp=84986707601&partnerID=8YFLogxK
U2 - 10.1002/jlac.1991199101146
DO - 10.1002/jlac.1991199101146
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AN - SCOPUS:84986707601
SN - 0170-2041
VL - 1991
SP - 851
EP - 856
JO - Liebigs Annalen der Chemie
JF - Liebigs Annalen der Chemie
IS - 9
ER -