Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by sulfur and silicon atom-containing group rearrangement

The intramolecular Diels-Alder reaction of furandiene with allenyl ethers followed by the rearrangement of sulfur and silicon atom-containing group were described. For the 5-(alkylthio)-2-furfuryl propargyl ethers, the alkylthio group 1,4-rearrangement products were exclusively derived and the alkylthio group 1,4-rearrangement occurred intramolecularly through tight ion pairs. For 5-(alkylsulfonyl)-2-furfuryl proparyl ethers and the 5-(alkylsulfinyl)-2-furfuryl proparyl ethers, alkylsulfonyl and alkylsulfinyl group 1,2-rearrangement products were derived, respectively.