Tetrahedron Letters p. 205 - 208 (1992)
Update date:2022-08-02
Topics:
Mayer, Theo
Maas, Gerhard
1-Morpholino-3-phenylallenes isomerize to 3,4,6,12b-tetrahydro-1H-<1,4>oxazino<4,3-a><2>benzazepines at >/= 105 deg C.Similarly, 1-morpholino-3-vinylallenes are transformed into 3,4,10,10a-tetrahydro-1H-<1,4>oxazino<4,3-a>azepines.Formation of these novel heterocycles is rationalized by a 1,3-proton shift in the morpholinoallenes, followed by 1,7-electrocylization of the α,β,γ,δ-unsaturated azomethine ylide thus formed.
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