Iodine(III)-Mediated Ring Contraction Reactions: Synthesis of Oxygen- and Nitrogen-Substituted Indanes

Journal of the Brazilian Chemical Society

Ahmad, Anees¹  Silva Júnior, Luiz F.¹  Universidade de São Paulo, São Paulo, Brazil¹ 

关键词:  indane;    hypervalent iodine;    ring contraction;    1;    2-dihydronaphthalenes;   

DOI  :  10.5935/0103-5053.20160065

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

The synthesis of oxygen- and nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71% yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77% yield. The tosyl-protected substrate resulted only in addition products.

【 授权许可】

Unknown