MODIFIED PREPARATION OF SODIUM GUAIAZULENIDE AND REACTION OF THE REAGENT WITH 3-FORMYLGUAIAZULENE

As a modification for facilitating small-scale reactions, sodium iV-methylanilinide was prepared from sodium hydride and iV-methylaniline instead of by the usual method from sodium, JV-methylaniline, and naphthalene (as assistant). Sodium iV-methylanilinide, made by this procedure, was successively converted to sodium guaiazulenide, the formation of which was checked by tracing known reactions. The reaction of the reagent with 3-formyl-guaiazulene was also studied, and found to yield 4-substituted 2-formyl-l, 4-dihydroguaiazulene and 6-substituted 2-formyl-3, 6-dihydroguaiazulene. In this case, nucleophilic addition of guaiazulenide anion occured not at the carbonyl group but at the 6- and 8-positions of the seven-membered ring of formylguaiazulene, accompanied by formyl group and hydrogen migrations.