92527-66-7Relevant academic research and scientific papers
A NEW METHOD FOR THE HYDROXYMETHYLATION OF CARBONYL COMPOUNDS
Imamoto, Tsuneo,Takeyama, Toshiaki,Yokoyama, Masataka
, p. 3225 - 3226 (1984)
Benzyl chloromethyl ether reacts with carbonyl compounds in the presence of SmI2 to afford alcohols (I), which are subsequently subjected to hydrogenolysis to yield diols (II).
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.
