Novel Application of an Electrooxidative Method for the Formation of a Tetrahydrofuran Ring from 5-Hydroxy-2-pentanone Phenylhydrazone
摘要:
Various ketone phenylhydrazones that possess a hydroxy group Oil the parent ketone moiety were subjected to electrooxidation in methanol ill the presence of KI and NaOMe. In the case of 4-hydroxy-2-butanone phenylhydrazone, the nucleophilic attack of the azomethine carbon by a methoxide ion affording the corresponding methoxy(phenylazo)alcohol was dominant. Interestingly, however, in the case of 5-hydroxy-2-pentanone phenylhydrazone, similar reaction conditions favored the intramolecular cyclization to afford a (phenylazo)tetrahydrofuran derivative.