Tetrahedron

Thermal rearrangement of benzisoxazole-and naphthisoxazolequinones in solution and in the solid state. Stereoselective synthesis of γ- …

MV Martínez-Díaz, S Rodríguez-Morgade, W Schäfer…

Index: Martinez-Diaz, M. Victoria; Rodriguez-Morgade, Salome; Schaefer, Wolfram; Torres, Tomas Tetrahedron, 1993 , vol. 49, # 11 p. 2261 - 2274

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Citation Number: 6

Abstract

Readily accessible benzisoxazolequinones 1 undergo thermal induced highly stereoselective rearrangement in solution to afford quantitatively γ- cyanomethylidenebutenolides 3. The transformation can be explained by the formation of a vinylogous nitrene intermediate 4, which undergoes an intramolecular acid-catalysed rearrangement. Compounds 3 react easily with alcohols in Michael addition. On the other ...