TY - JOUR
T1 - Photochemical transformations. Part 36. Synthesis and photolytic ring contraction of mesoionic 2-Alkylthiothiazol-4-ones; a new route to β-lactams
AU - Barton, Derek H.R.
AU - Buschmann, Ernst
AU - Hausler, Johannes
AU - Holzapfel, Cedric W.
AU - Sheradsky, Tuvia
AU - Taylor, Derryck A.
PY - 1977
Y1 - 1977
N2 - A number of mesoionic 2-alkylthiothiazol-4-ones (6) were prepared by alkylation of rhodanines or by the reaction of α-bromomalonates with dithiocarbamates. The photolysis of these mesoionic compounds proceeds via a highly strained, bicyclic, ring contraction product which rearranges to a thiazolin-2-one (14), loses sulphur, affording a β-aminoacrylate (11), or is trapped by methanol giving methoxy-β-lactams (12) and (13).
AB - A number of mesoionic 2-alkylthiothiazol-4-ones (6) were prepared by alkylation of rhodanines or by the reaction of α-bromomalonates with dithiocarbamates. The photolysis of these mesoionic compounds proceeds via a highly strained, bicyclic, ring contraction product which rearranges to a thiazolin-2-one (14), loses sulphur, affording a β-aminoacrylate (11), or is trapped by methanol giving methoxy-β-lactams (12) and (13).
UR - http://www.scopus.com/inward/record.url?scp=37049092535&partnerID=8YFLogxK
U2 - 10.1039/p19770001107
DO - 10.1039/p19770001107
M3 - Article
AN - SCOPUS:37049092535
SN - 1472-7781
SP - 1107
EP - 1114
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 9
ER -