ELECTRON-TRANSFER REACTIONS IN PULPING SYSTEMS .9. REACTIONS OF SYRINGYL ALCOHOL WITH PULPING REAGENTS

Syringyl alcohol was heated at 135-degrees-C in IM NaOH in the presenc e of anthrahydroquinone, sodium hydrosulfide, and glucose. Dimerizatio n 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 quino ne methide radical anion intermediates. Sodium sulfide reacted as a nu cleophile, rather than an electron transfer agent.