RING-CLEAVAGE OF 1-ALKYL-2-ARYL-3-(HYDROXYMETHYL)PYRROLIDINES - A PM3SEMIEMPIRICAL STUDY OF MOLECULAR MECHANISM

Authors
ROSENDE EG DOMINGO LR SEPULVEDAARQUES J MARMOL DP GARCIA EZ ACEROALARCON A SOLESIO BY
Citation
Eg. Rosende et al., RING-CLEAVAGE OF 1-ALKYL-2-ARYL-3-(HYDROXYMETHYL)PYRROLIDINES - A PM3SEMIEMPIRICAL STUDY OF MOLECULAR MECHANISM, Perkin transactions. 2, (3), 1997, pp. 643-648
Citations number
17
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Perkin transactions. 2 → ACNP
ISSN journal
03009580
Issue
3
Year of publication
1997
Pages
643 - 648
Database
ISI
SICI code
0300-9580(1997):3<643:RO1-AP>2.0.ZU;2-W
Abstract
A fragmentation reaction at room temperature takes place when 2-aryl-3 -(hydroxymethyl)-1-methylpyrrolidines react with different arenesulfon yl chlorides and triethylamine. A PM3 semiempirical study of the fragm entation reaction of the quaternary benzenesulfonamide salt of 1-methy l-2-phenyl-3-(hydroxymethyl)pyrrolidine shows that the reaction procee ds by a stepwise mechanism through the formation of a benzylic cation.