Electron Transfer Reactions in Pulping Systems IX. Reactions of Syringyl Alcohol with Pulping Reagents

Abstract

Syringyl alcohol was heated at 135° in 1M NaOH in the presence of anthrahydroquinone, sodium hydrosulfide, and glucose. Dimerization of syringyl alcohol to disyringylmethane was suppressed by all three reagents. An analysis of the types and amounts of products formed at various times indicated (1) that the reagents reacted reversibly with intermediate quinone methides and (2) that electron transfer reactions occurred in the cases of anthrahydroquinone and glucose to give quinone methide radical anion intermediates. Sodium sulfide reacted as a nucleophile, rather than an electron transfer agent.