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 journalArticlepeer-review

15 Citations (Scopus)

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 languageEnglish
Pages (from-to)3107-3112
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number20
DOIs
Publication statusPublished - 21 Oct 1997

Keywords

  • RING

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