The effect of the phenylhydrazine moiety on the substitution at the carbonyl residue in phenylhydrazones of isohydrocoriamyrtin and allethrolone

Abstract

The effect of the phenylhydrazine moiety at C-14 over the substitution reaction of the allylic OH group at C-11 in isohydrocoriamyrtin phenylhydrazone and analogues has been studied in an attempt to prove the participation of this effect in the formation of the unusual reaction product II. Marked influence of the substituents on the Ph ring of the phenylhydrazine moiety across -NH-N= bond was shown by the comparison of the methoxylation of phenylhydrazone and α-methyl-, p-nitro-,2,4-dinitro-, and α-methyl-2,4-dinitro-phenylhydrazone of isohydrocoriamyrtin. The methoxylation of o-nitro-, p-nitro-, and 2,4-dinitro-phenylhydrazone of allethrolone also showed appreciable effect by each group on the Ph ring.