TY - JOUR
T1 - Ozonolyses of Acetylenes
T2 - Trapping of α-Oxo Carbonyl Oxides by Carbonyl Compounds and Stabilization of α-Oxo Ozonides by Derivatizations
AU - Griesbaum, Karl
AU - Dong, Yuxiang
AU - McCullough, Kevin J.
PY - 1997
Y1 - 1997
N2 - Ozonolyses of 2-butyne (7) or of 3-hexyne (14) in the presence of carbonyl compounds (aldehydes, ketones, acid derivatives) afforded the corresponding mostly labile monocyclic α-oxo ozonides (9, 13a, 16), which could be stabilized and, hence, isolated by subsequent conversion into α-methoximino derivatives. Ozonolyses of 1,4-diacyloxy-substituted (19) and 1-acyloxy-substituted 2-butynes (27) gave bicyclic ozonides (22,31) by intramolecular [3 + 2]-cycloadditions of the corresponding carbonyl oxide intermediates (20, 29). These ozonides could also be stabilized by reactions with O-methylhydroxylamine to give O-methyloximes (23c, 32) or with diazomethane to give epoxy ozonides (25, 34).
AB - Ozonolyses of 2-butyne (7) or of 3-hexyne (14) in the presence of carbonyl compounds (aldehydes, ketones, acid derivatives) afforded the corresponding mostly labile monocyclic α-oxo ozonides (9, 13a, 16), which could be stabilized and, hence, isolated by subsequent conversion into α-methoximino derivatives. Ozonolyses of 1,4-diacyloxy-substituted (19) and 1-acyloxy-substituted 2-butynes (27) gave bicyclic ozonides (22,31) by intramolecular [3 + 2]-cycloadditions of the corresponding carbonyl oxide intermediates (20, 29). These ozonides could also be stabilized by reactions with O-methylhydroxylamine to give O-methyloximes (23c, 32) or with diazomethane to give epoxy ozonides (25, 34).
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U2 - 10.1021/jo9701795
DO - 10.1021/jo9701795
M3 - Article
AN - SCOPUS:0001495579
SN - 0022-3263
VL - 62
SP - 6129
EP - 6136
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -