Thermal transformations of oxazole endoperoxides: Rearrangements, fragmentations and methanol additions
作者:Klaus Gollnick、Sigrid Koegler
DOI:10.1016/0040-4039(88)85320-6
日期:1988.1
Oxazole endoperoxides carrying a phenyl group at C-2 rearrange to triacylamines ; those carrying a hydrogen atom at C-2 undergo a fragmentation into 1:1 mixtures of nitriles (or HCN) and anhydrides , whereas methyl substitution at C-2 gives rise to competition between these two modes of reaction. Methanol addition to leads to4-methoxy-5-hydroperoxides which easily transform into methyl esters and diacylamines
在C-2带有苯基的恶唑内过氧化物重排为三酰基胺; 那些在C-2处带有氢原子的化合物会碎裂成腈(或HCN)和酸酐的1:1混合物,而C-2处的甲基取代会引起这两种反应方式之间的竞争。甲醇加成后会生成4-甲氧基-5-氢过氧化物,容易转化为甲酯和二酰基胺。