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Ozonolyses of O ‐methyloximes in the presence of acid derivatives: A new access to substituted ozonides
Author(s) -
Griesbaum Karl,
Övez Bikem,
Huh Tae Sung,
Dong Yuxiang
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199508217
Subject(s) - chemistry , trifluoroacetic acid , ozonolysis , oxime , acetone , organic chemistry , medicinal chemistry
Ozonolyses of O ‐methyloximes ( 4 ) of 5‐, 6‐ and 7‐membered cycloketones in the presence of esters of trifluoroacetic acid ( 5 ) or of acyl cyanides ( 6 ) afforded ozonides of types 7 and 8 , respectively, which are formally derived from vinyl ethers or vinyl cyanides. Similarly, ozonolysis of the O ‐methylated oxime of acetone ( 9 ) in the presence of esters of trifluoroacetic acid ( 5 ) and of the O ‐methylated oxime of 2‐naphthaldehyde ( 11 ) in the presence of acyl cyanides ( 6 ) gave the corresponding ozonides of types 10 and 12 , respectively.