The reaction of carbonyl compounds with diiodomethane in the presence of samarium: Novel syntheses of iodohydrins and cyclopropanols
β Scribed by Tsuneo Imamoto; Toshiaki Takeyama; Hiroyasu Koto
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 229 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Sumnary: The iodomethylation of carbonyl compounds giving iodohydrins has been achieved under ordinary conditions by the use of diiodomethane and samarium. A novel synthesis of cyclopropanols from d-haloketones or 1,2-dibenzoylethane is also described. Nucleophilic halomethylations of carbonyl compounds provide synthetically useful halohydrins and related compounds. ations which can be conducted at Several research groups hf;e established di-and trihalomethylaround room temperature. In co2n)trast, monohalomethylation
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The treatment of isomeric vinylic tellurides 5-7with butyllithium in THF at -78 Β°C in the presence of a carbonyl compound such as benzaldehyde or cyclohexanone was studied High selectivity of the attack at the tellurium atom was observed. In most cases, the corresponding allylic alcohol was obtained
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