TY - JOUR
T1 - New 1,3,4-thiadiazolium-3-(unsubstituted) methanide 1,3-dipoles (azolium 1,3-dipoles)
T2 - Useful synthons at -60°C: A new ring interconversion route to 1,2,3-trisubstituted and 1,2,3,4-tetrasubstituted 1-{[1-(vinylthio)-1-phenylmethylidene]amino}pyrroles
AU - Butler, Richard N.
AU - Cloonan, Martin O.
AU - McArdle, P.
AU - Cunningham, D.
PY - 1998/4/7
Y1 - 1998/4/7
N2 - 1,3,4-Thiadiazolium-3-(unsubstituted) methanides have been trapped with substituted alkyne dipolarophiles at -60°C giving high yields of 2,3-di- and 2,3,4-tri-substituted 1-{[1-(vinylthio)-1-phenylmethylidene]amino}pyrroles from a cycloaddition rearrangement sequence. The conformation of these molecules results in an unusual proton shielding effect in the 1H NMR spectra. An X-ray crystal structure is reported for methyl 1-{(Z)-1-[(Z)-2-methoxycarbonylvinylthiol-1-phenylmethylideneamino}-2-phenyl-1H- pyrrole-3-carboxylate 7a.
AB - 1,3,4-Thiadiazolium-3-(unsubstituted) methanides have been trapped with substituted alkyne dipolarophiles at -60°C giving high yields of 2,3-di- and 2,3,4-tri-substituted 1-{[1-(vinylthio)-1-phenylmethylidene]amino}pyrroles from a cycloaddition rearrangement sequence. The conformation of these molecules results in an unusual proton shielding effect in the 1H NMR spectra. An X-ray crystal structure is reported for methyl 1-{(Z)-1-[(Z)-2-methoxycarbonylvinylthiol-1-phenylmethylideneamino}-2-phenyl-1H- pyrrole-3-carboxylate 7a.
UR - https://www.scopus.com/pages/publications/33748832942
U2 - 10.1039/a708010g
DO - 10.1039/a708010g
M3 - Article
SN - 0300-922X
SP - 1295
EP - 1297
JO - Journal of the Chemical Society - Perkin Transactions 1
JF - Journal of the Chemical Society - Perkin Transactions 1
IS - 7
ER -