ORGN 72 |
| Jong Kwan Bin1, Jae Sang Lee1, and Kyongtae Kim2. (1) School of Chemistry and Molecular Engineering, Seoul National University, Shillim dong, Kwanak gu, Seoul, 151-742, South Korea, (2) Department of Chemistry, Seoul National University, Shillim dong, Kwanak gu, Seoul, 151-742, South Korea |
| The enolate anions derived from α-ketosulfones have considerable potential for use in synthetic sequences requiring monoalkylation. However, regiospecific or regioselective alkylations of α-ketosulfones, bis(methylsulfonyl)methane, and α-ketosulfoxides, etc, have been an important subject in organic synthesis. We have found that treatment of 2,2-bis(alkylsulfonyl)-1-phenylethanone 1 with LDA (2 equiv.) for 5 min in THF at room temperature afforded 2-substituted 2-alkylsulfonylmethylsulfonyl-1-phenylethanones 2 in 45-90% yields. Similar treatment of 2,2-bis(methylsulfonyl)-2-methyl-1-phenyl-1-propanone 3 under the same conditions gave 2-[(1-methylsulfonyl)ethylsulfonyl]-1-phenylethanone 4 in 69% yield. However, [2-bis(methylsulfonyl)-1-methoxy]ethylbenzene 5 was quantitatively recovered from its reaction with LDA under the same conditions. A plausible mechanism for the rearrangement reaction will be discussed. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |
