Indium-mediated, highly efficient cyclopropanation of olefins using CH 2I 2 as methylene transfer reagent

Tetrahedron Letters

Volumn 46, Issue 1, 2005, Pages 37-38

  Virender, ^a   Jain, Suman L ^a   Sain, Bir ^a  

^a CSIR INDIAN INSTITUTE OF PETROLEUM   (India)

Author keywords

Cyclopropanation; Indium; Methylene iodide; Methylene transfer; Olefins

Indexed keywords

ALKENE DERIVATIVE; CARBENE; INDIUM; IODINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOPROPANATION; REACTION ANALYSIS;

EID: 9944251982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.047     Document Type: Article

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35. Typical experimental procedure: To a stirred mixture of cyclohexene (82 mg, 1 mmol) and indium metal (114 mg, 1 mmol) in acetonitrile (5 ml) was added methylene iodide (320 mg, 1.2 mmol) drop by drop under a nitrogen atmosphere at 25°C. Stirring was continued until the reaction mixture appeared turbid. After completion, the reaction mixture was filtered followed by evaporation of the solvent. The residue obtained was purified by passing through a short silica gel column using hexane/ethyl acetate (4:1) as eluent. Evaporation of the solvent yielded bicyclo[4.1.0]heptane (86 mg, 92%). Other cyclopropanes were prepared similarly, their reaction times and yields are presented in the Table 1
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