We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
(Benzylthio)- und (Arylthio)-substituierte Nitril-ylide: Thermische Erzeugung und Reaktionen.
- Authors
Wipf, Peter; Prevo, Roland; Bieri, Jost H.; Germain, Gabriel; Heimgartner, Heinz
- Abstract
Thermal Generation and Reactions of (Benzylthio)-and (Arylthio)-Substituted Nitrile Ylides Thermolysis of 4-(benzylthio)- and 4-(arylthio)-1,3-oxazol-5(2 H)-ones 6, at 110-155° in the presence of dipolarophiles with activated C≡C, CC, CO, CS, and NN bonds, led to 5-membered cyclo-adducts and CO2 ( cf. Schemes 3, 5-7). Heating 6a and 6c in the presence of ethyl propiolate yielded ethyl quinoline-3-carboxylate ( 19) and ethyl pyridine-3-carboxylate( 22), respectively ( cf. Scheme 8). These results are rationalized on the basis of the intermediate formation of thio-substituted nitrile ylides of type 7 ( cf. Scheme 2), which undergo regioselective 1,3-dipolar cycloadditions with reactive dipolarophiles. In the absence of such a dipolarophile, the nitrile ylides isomerize via a [1,4]-H shift to give 2-aza-1,3-butadienes of type 20. The latter are trapped in a Diels- Alder reaction with ethyl propiolate ( cf. Scheme 8).
- Publication
Helvetica Chimica Acta, 1988, Vol 71, Issue 5, p1177
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19880710529