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(Benzylthio)- und (Arylthio)-substituierte Nitril-ylide: Thermische Erzeugung und Reaktionen by Peter Wipf; Roland Prevo; Jost H. Bieri; Gabriel Germain; Heinz Heimgartner is a Chemistry article available to read on EtoBox.

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## Thermal Generation and Reactions of (Benzy1thio)-and (Ary1thio)-Substituted Nitrile Ylides Thermolysis of 4-(benzy1thio)-and 4-(ary1thio)-1,3-oxazol-5(2H)-ones 6, at 1 10-1 55" in the presence of dipolarophiles with activated CEC, C=C, C=O, C=S, and N=N bonds, led to 5-membered cyclo-adducts and C 0 2 (el: 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 uia 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). ' ) Einige Nitril-ylide ii mit R' = PhN(CH,) sind R2 .

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Author

Peter Wipf; Roland Prevo; Jost H. Bieri; Gabriel Germain; Heinz Heimgartner

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

1988

Language

DE

Field

Chemistry (Physical Sciences)