Tetrahedron

Chemistry of pyrrolizines; reactions with cyanogen bromide and trifluoroacetic anhydride

W Verboom, GW Visser, DN Reinhoudt

Index: Verboom,W.; Visser,G.W.; Reinhoudt,D.N. Tetrahedron, 1982 , vol. 38, p. 1831

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Citation Number: 6

Abstract

Interaction of the pyrrolizine 3 with cyanogen bromide in a tetrahydrofuran/water mixture affords addition to the enamine double bond with formation of 5 which can be aromatized to 6 by silica gel. Reaction of 6 with cyanogen bromide in the same solvent mixture yields the indoline 8a which structure is proved in a chemical way by conversion of the product into the aldehyde 8d. The different reaction pathway is discussed in terms of steric hindrance by ...