- 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
-
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.
- Imamoto, Tsuneo,Hatajima, Toshihiko,Takiyama, Nobuyuki,Takeyama, Toshiaki,Kamiya, Yasuo,Yoshizawa, Takeshi
-
p. 3127 - 3135
(2007/10/02)
-
- A NEW METHOD FOR THE HYDROXYMETHYLATION OF CARBONYL COMPOUNDS
-
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).
- Imamoto, Tsuneo,Takeyama, Toshiaki,Yokoyama, Masataka
-
p. 3225 - 3226
(2007/10/02)
-