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Formation of Allenyl Ketones, 3‑Ethynylcoumarins, and Arylfurans,
Furylfurans, and Furylthiophenes by Flash Vacuum Thermolysis of
3‑Methylidenefuran-2(3H)‑ones
ABSTRACT: Flash vacuum thermolysis (FVT) of 3-methylidenefuran-2(3H)-
ones 3 causes cheletropic extrusion of CO with formation of allenyl ketones 4.
o-Chloro- and o-bromophenylmethylidenefuranones also afford allenyl ketones
upon flash vacuum thermolysis, but in addition, 3-ethynylcoumarins 6 are
formed via E/Z isomerization of the methylidenefuranones, cyclization,
halogen atom migration, and HCl (HBr) elimination. The presence of
strongly electron-withdrawing groups (nitroaryl or acetyl) on the acylallene
moiety causes rearrangement to give 2-arylfurans 10 and 13 as well as 2-
furylfurans and 2-furylthiophenes 16 by cyclization of the allenyl ketones. The
reaction mechanisms are supported by calculations at the M06-2X/6-
311+G(d,p) level of theory.

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