163230-08-8Relevant academic research and scientific papers
Structural studies of a novel heterocyclic phosphorane
Gabbutt, Christopher D.,Hepworth, John D.,Heron, B. Mark,Jones, Alan M.,Raper, Eric S.,Clegg, William
, p. 221 - 230 (1998)
Reaction of 2,2,6-trimethylthiochroman-3,4-dione with an excess of methylenetriphenyl-phosphorane yields the stabilised ylide (4) by way of an α-ketol rearrangement. X-Ray crystallography indicates that (4) exists as the (Z)-isomer and provides supporting evidence for an enolate structure.
The Reaction of Methylidenetriphenylphosphorane with Aromatic and Heterocyclic 1,2-Diketones.
Gabbutt, Christopher D.,Hepworth, John D.,Heron, B. Mark
, p. 805 - 819 (2007/10/02)
Treatment of both 2,2,6-trimethylthiochromane-3,4-dione (1a) and 3,3,6,8-tetramethyl-1,2,3,4-tetrahydronaphthalene-1,2-dione (1b) with one equivalent of Ph3P=CH2 affords a 1,2-methylidene ketone (3).Reaction with a further mole of the ylide gives a 1,2-diphenylphosphinoylethyl ketone (7) by a Michael addition and elimination of benzene.When the diketones (1a and 1b) are treated directly with two moles of the ylide, ring contraction occurs by an α-ketol rearrangement and a resonance stabilised ylide (10) results.Whereas benzil yields only diphenylbutadiene with anexcess of the ylide, 9,10-phenanthraquinone gives an α-hydroxyketone (15).
