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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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