Trialkylamine-mediated intramolecular acylation of alkenes with carboxylic acid chlorides.
Trialkylamine-mediated intramolecular cyclization of pent-4-enoyl chlorides was studied. Substitution with a tertiary alkyl group at the 2-position gave cyclopent-2-en-1-ones, while substitution with an aromatic group gave enol esters, which were formed by O-acylation of initially formed 3-chlorocyclopentanones with ketenes.
Matsuo
Jun-ichi
J
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Japan. jimatsuo@p.kanazawa-u.ac.jp
Hoshikawa
Takaya
T
Sasaki
Shun
S
Ishibashi
Hiroyuki
H
D000215:Acylation; D000475:Alkenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*
D000475:Alkenes; D002264:Carboxylic Acids; D002712:Chlorides; D005030:Ethylenes; D007659:Ketones; C008223:ketene