Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction

Journal of the Brazilian Chemical Society

Luiz F. Silva Jr.²  Samir A. P. Quintiliano²  Helena M. C. Ferraz²  Leonardo S. Santos¹  Marcos N. Eberlin¹ 

[1] ,Universidade de São Paulo Instituto de Química São Paulo SP ,Brazil

关键词: thallium trinitrate;    ring contraction;    homoallylic alcohols;    fragmentation reaction;    indan;   

DOI  :  10.1590/S0103-50532006000500024

来源: SciELO

【 摘 要 】

The oxidation of tertiary homoallylic alcohols with thallium trinitrate (TTN) was investigated. The alcohols bearing an allylic methyl group lose a molecule of acetone via a fragmentation reaction that leads to isomeric secondary allylic alcohols as major products, together with their corresponding acetylated derivatives. On the other hand, treating analogous tertiary alcohols without the allylic methyl group with TTN gives indans, through a ring contraction reaction.

【 授权许可】

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