Journal of the Chemical Society. Perkin transactions I p. 485 - 489 (1996)
Update date:2022-08-05
Topics:
Aitken, R. Alan
Herion, Hugues
Horsburgh, Caroline E. R.
Karodia, Nazira
Seth, Shirley
Seven examples of the alkynoyl phosphorus ylides 5 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 750°C, to undergo extrusion of Ph3PO to give the unsymmetrical 1,3-diynes 9 in moderate yield. Six examples of the oxalyl diylides 6 have been prepared and their fully assigned 13C NMR spectra are presented. Upon FVP, those with R = aryl undergo two-fold extrusion of Ph3PO to give symmetrical 1,3-diynes 13 but this requires the unusually severe temperature of 900°C. In contrast those with R = CO2Me, CO2Et or COPh undergo complete reaction at 500°C but afford only Ph3PO and fragmentation products.
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