TY - JOUR
T1 - Flash vacuum pyrolysis of stabilised phosphorus ylides .8. Preparation of symmetrical and unsymmetrical 1,3-diynes from alkynoyl ylides and oxalyl diylides
AU - Aitken, R Alan
AU - Herion, H
AU - Horsburgh, C E R
AU - Karodia, N
AU - Seth, S
PY - 1996/3/7
Y1 - 1996/3/7
N2 - Seven examples of the alkynoyl phosphorus ylides 5 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 750 degrees C, to undergo extrusion of Ph(3)PO 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 C-13 NMR spectra are presented. Upon FVP, those with R = aryl undergo two-fold extrusion of Ph(3)PO to give symmetrical 1,3-diynes 13 but this requires the unusually severe temperature of 900 degrees C. In contrast those with R = CO(2)Me, CO(2)Et or COPh undergo complete reaction at 500 degrees C but afford only Ph(3)PO and fragmentation products.
AB - Seven examples of the alkynoyl phosphorus ylides 5 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 750 degrees C, to undergo extrusion of Ph(3)PO 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 C-13 NMR spectra are presented. Upon FVP, those with R = aryl undergo two-fold extrusion of Ph(3)PO to give symmetrical 1,3-diynes 13 but this requires the unusually severe temperature of 900 degrees C. In contrast those with R = CO(2)Me, CO(2)Et or COPh undergo complete reaction at 500 degrees C but afford only Ph(3)PO and fragmentation products.
UR - http://www.scopus.com/inward/record.url?scp=1542398199&partnerID=8YFLogxK
U2 - 10.1039/p19960000485
DO - 10.1039/p19960000485
M3 - Article
SN - 0300-922X
SP - 485
EP - 489
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 5
ER -