Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 11. Unexpected generation and rearrangement of acetyl benzotriazolyl carbene

Robert Alan Aitken; IM Fairhurst; A Ford; PE Milne; DW Russell; M Whittaker

doi:10.1039/A604594D

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 11. Unexpected generation and rearrangement of acetyl benzotriazolyl carbene

Robert Alan Aitken
, IM Fairhurst
, A Ford
, PE Milne
, DW Russell
, M Whittaker

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	3107-3112
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	20
DOIs	https://doi.org/10.1039/A604594D
Publication status	Published - 21 Oct 1997

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title = "Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 11. Unexpected generation and rearrangement of acetyl benzotriazolyl carbene",

abstract = "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.",

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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 - https://www.scopus.com/pages/publications/33748669661

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 -

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 11. Unexpected generation and rearrangement of acetyl benzotriazolyl carbene

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