REARRANGEMENT OF CIS-1-METHYL-2-(2-THIENYL)PYRROLIDINIUM AND TRANS-1-METHYL-2-(2-THIENYL)PYRROLIDINIUM 1-METHYLIDES IN A NON-BASIC MEDIUM

Authors
KAWANISHI N FUJIWARA K SHIRAI N SATO Y HATANO K KURONO Y
Citation
N. Kawanishi et al., REARRANGEMENT OF CIS-1-METHYL-2-(2-THIENYL)PYRROLIDINIUM AND TRANS-1-METHYL-2-(2-THIENYL)PYRROLIDINIUM 1-METHYLIDES IN A NON-BASIC MEDIUM, Journal of the Chemical Society. Perkin transactions. I, (20), 1997, pp. 3013-3016
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
20
Year of publication
1997
Pages
3013 - 3016
Database
ISI
SICI code
0300-922X(1997):20<3013:ROCAT>2.0.ZU;2-B
Abstract
cis-1-Methyl-2-(2-thienyl)pyrrolidinium 1-methylide cis-2 generated in a non-basic medium isomerize to a mixture of (E)- and -methyl-3a,4,5, 6,7,8-hexahydrothien[3,2-c]azocine, (E)-6 and (Z)-6. The latter (Z)6 h as been cyclized to the thyl-3a,6,7,8,8a,8b-hexahydro-4H-thienol[2',3' -c]- pyrrolo[1,2-a]pyrrolium salt 8 in water; trans-2 gives a mixture of 1-methyl-3-(2-thienyl)piperidine 7 and (E)-6 via a radical-cleavage and -recombination pathway.