Ring contraction of N-chlorolactams, a novel rearrangement |
| |
Authors: | Alexandre Drouin |
| |
Institution: | Département de Chimie, Université de Sherbrooke, 2500 Boul. Univsersité, Sherbrooke, Québec, Canada J1K 2X9 |
| |
Abstract: | Upon photolysis in methylene chloride at −78 °C, different N-chlorolactams underwent a novel ring contraction to the corresponding carbamoyl chlorides, which were converted to the methyl carbamates. The rearrangement is 100% stereoselective, occurring with retention of configuration at the migrating carbon center. The yields of isolated carbamates ranged from 40% to 57%, the other product being the parent lactam, 18% to 38%. |
| |
Keywords: | N-Chlorolactams Nitrogen-heterocycles Photolysis Rearrangement Ring contraction |
本文献已被 ScienceDirect 等数据库收录! |
|