Tetrahedron Letters p. 1007 - 1010 (1988)
Update date:2022-08-05
Topics: Nitrile Thermal rearrangements Anhydride Ring Expansion Homolytic Cleavage Heterolytic Cleavage
Gollnick, Klaus
Koegler, Sigrid
Oxazole endoperoxides 1 carrying a phenyl group at C-2 rearrange to triacylamines 3; those carrying a hydrogen atom at C-2 undergo a fragmentation into 1:1 mixtures of nitriles (or HCN) 4 and anhydrides 5, whereas methyl substitution at C-2 gives rise to competition between these two modes of reaction.Methanol addition to 1 leads to 4-methoxy-5-hydroperoxides 6 which easily transform into methyl esters 7 and diacylamines 8.
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(1988)
