2-Alkenylfurans react with phenylchlorocarbene to give furyl-gem-phenylchlorocyclopropanes.
Reduction of the furyl-gem-phenylchlorocyclopropanes with sodium in liquid ammonia leads to hydrogenolysus of the cyclopropane ring with the formation of 1-furyl-3-phenylalkanes.
The catalytic hydrogenation of the furyl-gem-phenylchlorocyclopropanes in a flow system over Pt/C at 260–265° leads to hydrogenolysis of both the furan and cyclopropane rings with the formation of phenyl-substituted ketones.
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The preliminary results are given in [1, 2]; also see .
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 379–384, February, 1976.
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Nefedov, O.M., Shostakovskii, V.M. & Kravchenko, M.I. Reaction of phenylchlorocarbene with 2-alkenylfurans and some transformations of the formed adducts. Russ Chem Bull 25, 359–364 (1976). https://doi.org/10.1007/BF00922475