Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III)

TETRAHEDRON LETTERS

卷:54

Article

Ahmad, Anees¹  Scarassati, Paulo¹  Jalalian, Nazli^1,2  Olofsson, Berit²  Silva, Luiz F., Jr.¹ 

[1] Univ Sao Paulo, Inst Quim, BR-05513970 Sao Paulo, Brazil

[2] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden

关键词: Rearrangement;    Hypervalent iodine;    Ring contraction;    Oxidation;    Alkenes;   

DOI  :  10.1016/j.tetlet.2013.08.012

来源: Elsevier

【 摘 要 】

A novel protocol for the oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III) was developed. This approach uses inexpensive, readily available, and stable chemicals (PhI, mCPBA, and TsOH) giving rearrangement products in yields comparable to those obtained using the more expensive commercially available [hydroxy(tosyloxy)iodo]benzene [HTIB or Koser's reagent]. Additionally, an alternative protocol for the synthesis of 1-methyl-2-tetralone through the one-step epoxidation/rearrangement of 4-methyl-1,2-dihydronaphthalene using mCPBA and TsOH was developed. (c) 2013 Elsevier Ltd. All rights reserved.

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