Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6??(Diisopropylamino)??1??azafulvene Derivatives. Novel synthesis of 5??mono??and 4, 5?? …

…, P Hess, JM Muchowski, ME Scheller

Index: Bray, Brian L.; Hess, Petr; Muchowski, Joseph M.; Scheller, Markus E. Helvetica Chimica Acta, 1988 , vol. 71, p. 2053 - 2057

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Citation Number: 14

Abstract

Abstract The first known lithiated 1-azafulvene derivatives were generated by low- temperature halogen/metal interchange, with t-BuLi, from the corresponding brominated 6- diisopropylamino compounds 3b and 12. These Li species reacted with sundry eletrophilic reagents to give products which, on basic hydrolysis, were converted into 5-mono-or 4, 5- disubstituted pyrrole-2-carbaldehydes 10 and 16, respectively.