COMPUTATIONAL STUDY ON ACID CATALYZED RING-OPENING REACTION OF 2,4-DIETHOXY-6-TRIFLUOROMETHYL-3,4-DIHYDRO-2H-PYRAN WITH THIOLS

[摘要]：2,4-Diethoxy-6-trifluoromethyl-3,4-dihydro-2H-pyran was reacted with thiols in the presence of p-toluenesulfonic acid by heating followed by treatment with trifluoroacetic acid to afford the corresponding 4-trifluoroacetyl-1,3-butadienyl sulfides selectively. Our DFT calculation results suggest thermodynamically controlled attack of thiols at 6-position of pyrylium intermediate followed by electrocyclic ring-opening as a reasonable mechanism for this reaction.

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