Tetrahedron letters

Zur 1, 3-thiazin-ringkontraktion: neue aspekte durch 6-donorsubstituenten

R Spitzner, W Schroth

Index: Spitzner, Roland; Schroth, Werner Tetrahedron Letters, 1985 , vol. 26, # 33 p. 3971 - 3974

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Abstract

Abstract The reaction of 6-morpholino-and 6-phenylthio-6H-1, 3-thiazines with buli at low temperature manifests striking differences to the behaviour of 2, 4, 6-triaryl species: ring contraction to the pyrrol ring system involves predominantly S-transfer into exocyclic position instead of immediate S-extrusion. The results are discussed in relation to π-donor effects by 6-heterosubstituents.

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