Conjugate addition of a phosphorus ylide to 3-cyanochromone

Gabbutt, C. D., Heron, B. M., Hursthouse, M. B. and Malik, K. M. A. (2000) Conjugate addition of a phosphorus ylide to 3-cyanochromone Phosphorus, Sulfur, and Silicon and the Related Elements, 166, pp. 99-109.


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Reaction of 3-cyanochromane with methylenetriphenylphosphorane yields the stabilised ylide (4) by way of a conjugate addition and subsequent ring opening. Variable temperature H-1 NMR spectroscopy indicates that this ylide undergoes rapid conformational interconversion at ambient temperature. X-ray crystallography established that (4) exists as the (E) isomer in the solid state.

Item Type: Article
Keywords: 3-cyanochromone, methylenetriphenylphosphorane, conjugate addition, x-ray crystallography, variable temperature h-1 nmr spectroscopy2-substituted chroman-4-ones, organophosphorus chemistry, structuralinvestigations, chromones, route, triphenylphosphine, hydroxylamine, reagents
ePrint ID: 19052
Date :
Date Event
Date Deposited: 19 Jan 2006
Last Modified: 16 Apr 2017 23:07
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