Tetrahedron letters

Thermal transformations of oxazole endoperoxides: Rearrangements, fragmentations and methanol additions

K Gollnick, S Koegler

Index: Gollnick, Klaus; Koegler, Sigrid Tetrahedron Letters, 1988 , vol. 29, # 9 p. 1007 - 1010

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Citation Number: 11

Abstract

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: l mixtures of nitriles (or HCN) 2 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 &methoxy-5- hydroperoxides 5 which easily transform into methyl esters z and diacylamines 2.

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