139152-85-5Relevant academic research and scientific papers
Reactions of Carbonyl Compounds with Benzyl Chloromethyl Ether of Diiodomethane in the Presence of Samarium(II) Iodide or Metallic Samarium. New Routes to 1,2-Diols, Iodohydrins and Cyclopropanols
Imamoto, Tsuneo,Hatajima, Toshihiko,Takiyama, Nobuyuki,Takeyama, Toshiaki,Kamiya, Yasuo,Yoshizawa, Takeshi
, p. 3127 - 3135 (2007/10/02)
Carbonyl compounds react with benzyl chloromethyl ether in the presence of samarium(II) iodide to afford the corresponding addition products which, when subsequently hydrogenolysed, yield 1,2-diols.Simple aldehydes and ketones react with diiodomethane in the presence of samarium metal to give iodohydrins in good yields.Under similar reaction conditions, α-halogeno substituted ketones and aromatic 1,4-diketones are converted into cyclopropanols.These cyclopropanations have been shown to rpoceed through the initial generation of samarium enolates, followed by the Simmons-Smith type reaction.A novel transformation of esters to cyclopropanols via tandem one-carbon homologation is also described.
