222178-82-7Relevant academic research and scientific papers
Photochemical and thermal ring-contraction of cyclic hydroxamic acid derivatives
Pichette, Simon,Aubert-Nicol, Samuel,Lessard, Jean,Spino, Claude
, p. 11216 - 11226 (2013/04/23)
Cyclic hydroxamic acids can undergo a thermal ring contraction after an in situ triflation. High yields of ring-contraction products are obtained with DBU when the migrating carbon is a methylene, while best results are obtained with Et3N for the migration of quaternary carbons. In some cases, the regiochemical outcome of the reaction can be controlled by changing the base. This novel thermal rearrangement complements a similar but photochemical rearrangement of N-mesyloxylactams.
Ring contraction of N-chlorolactams, a novel rearrangement
Drouin, Alexandre,Lessard, Jean
, p. 4285 - 4288 (2007/10/03)
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%.
REACTIONS OF CARBAMYL RADICALS: INTRAMOLECULAR HYDROGEN ABSTRACTION REACTIONS
Dicks, Patrick F.,Glover, Steohen A.,Goosen, Andre,McCleland, Cedric W.
, p. 923 - 934 (2007/10/02)
ω-Phenylalkyl-N-methylcarbamyl radicals undergo intermolecular addition to 3,3-dimethylbut-1-ene in preference to intramolecular hydrogen abstraction.Methyl N-(ω-phenylalkyl) carbamyl radicals and methyl N-pentylcarbamyl radicals readily abstract hydrogen
