The reactions of 2,3-dihydro-2-methylene-1,3,3-trimethyl-1 H-indole (Fischer’s base) with nitro-olefins and alkoxy- nitro-olefins have been examined. Formation of the corresponding Michael-type adducts has been observed in all cases with the exception of 2-nitropropene for which the spiro- 1,2-oxazine N-oxide derivative could be isolated. The Michael-ty pe adducts derived from alkoxy- nitro-olefins underwent a rapid elimination reaction resulting in the eventual formal nitro-olefination of the Fischer’s base. The geometry of the products has been determined by means of DIFNOE experiments and their UV properties have been examined.

Reactions of Fischer's base with cyclic and acyclic conjugated nitroolefins and nitrovinylethers

FELLUGA, FULVIA;FORZATO, Cristina;NITTI, PATRIZIA;PITACCO, GIULIANA;VALENTIN, ENNIO
2002

Abstract

The reactions of 2,3-dihydro-2-methylene-1,3,3-trimethyl-1 H-indole (Fischer’s base) with nitro-olefins and alkoxy- nitro-olefins have been examined. Formation of the corresponding Michael-type adducts has been observed in all cases with the exception of 2-nitropropene for which the spiro- 1,2-oxazine N-oxide derivative could be isolated. The Michael-ty pe adducts derived from alkoxy- nitro-olefins underwent a rapid elimination reaction resulting in the eventual formal nitro-olefination of the Fischer’s base. The geometry of the products has been determined by means of DIFNOE experiments and their UV properties have been examined.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11368/1702452
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