TY - JOUR
T1 - Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 11. Unexpected generation and rearrangement of acetyl benzotriazolyl carbene
AU - Aitken, Robert Alan
AU - Fairhurst, IM
AU - Ford, A
AU - Milne, PE
AU - Russell, DW
AU - Whittaker, M
PY - 1997/10/21
Y1 - 1997/10/21
N2 - Seventeen novel alpha-benzotriazolyl-beta-oxo phosphorus ylides 2 have been prepared and characterised. Flash vacuum pyrolysis (FVP) of these generally leads to loss of both (R3PO)-P-1 and N-2 to give intractable products but, in one case, 21, extrusion of Bu3P is observed to give 3-acetyl-1,2,4-benzotriazine 6 and 2'-cyanoacetophenone 7, products apparently derived from rearrangement of the initially formed carbene 11, and involving in the latter case a novel 1,3-acetyl migration process.
AB - Seventeen novel alpha-benzotriazolyl-beta-oxo phosphorus ylides 2 have been prepared and characterised. Flash vacuum pyrolysis (FVP) of these generally leads to loss of both (R3PO)-P-1 and N-2 to give intractable products but, in one case, 21, extrusion of Bu3P is observed to give 3-acetyl-1,2,4-benzotriazine 6 and 2'-cyanoacetophenone 7, products apparently derived from rearrangement of the initially formed carbene 11, and involving in the latter case a novel 1,3-acetyl migration process.
KW - RING
UR - http://www.scopus.com/inward/record.url?scp=33748669661&partnerID=8YFLogxK
U2 - 10.1039/A604594D
DO - 10.1039/A604594D
M3 - Article
SN - 0300-922X
SP - 3107
EP - 3112
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 20
ER -