Abstract
Alkylfuryl alcohols, particularly 5-hydroxymethyl-2-methylfuran, produce bis(5-alkyl-2-furyl)methane and related ethers when exposed to hydrothermolytic or pyrolytic conditions. The hydrothermolytic route to the di(furyl)methane appears to proceed through a carbonium ion intermediate. However, a triene intermediate, obtained via dehydration, cannot be overlooked for the pyrolytic mechanism. The dimer was detected in condensed cigarette smoke.
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