THERMAL TRANSFORMATIONS OF OXAZOLE ENDOPEROXIDES: REARRANGEMENTS, FRAGMENTATIONS AND METHANOL ADDITIONS

DOI: 10.1016/0040-4039(88)85320-6

Source and publish data:

Tetrahedron Letters p. 1007 - 1010 (1988)

Update date:2022-08-05

Topics: Nitrile Thermal rearrangements Anhydride Ring Expansion Homolytic Cleavage Heterolytic Cleavage

Authors:

Gollnick, Klaus

Koegler, Sigrid

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Article abstract of DOI:10.1016/0040-4039(88)85320-6

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.

Full text of DOI:10.1016/0040-4039(88)85320-6

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