Conjugate addition of a phosphorus ylide to 3-cyanochromone

Christopher D. Gabbutt; B. Mark Heron; Michael B. Hursthouse; K. M. Abdul Malik

doi:10.1080/10426500008076534

Conjugate addition of a phosphorus ylide to 3-cyanochromone

Christopher D. Gabbutt, B. Mark Heron, Michael B. Hursthouse, K. M. Abdul Malik

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

4 Citations (Scopus)

Abstract

Reaction of 3-cyanochromone with methylenetriphenylphosphorane yields the stabilised ylide (4) by way of a conjugate addition and subsequent ring opening. Variable temperature ¹H 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.

Original language	English
Pages (from-to)	99-109
Number of pages	11
Journal	Phosphorus, Sulfur and Silicon and Related Elements
Volume	166
Issue number	1
DOIs	https://doi.org/10.1080/10426500008076534
Publication status	Published - 1 Jan 2000
Externally published	Yes

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abstract = "Reaction of 3-cyanochromone with methylenetriphenylphosphorane yields the stabilised ylide (4) by way of a conjugate addition and subsequent ring opening. Variable temperature 1H 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.",

keywords = "3-cyanochromone, Conjugate addition, Methylenetriphenylphosphorane, Variable temperature H NMR spectroscopy, X-ray crystallography",

author = "Gabbutt, {Christopher D.} and Heron, {B. Mark} and Hursthouse, {Michael B.} and {Abdul Malik}, {K. M.}",

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AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Hursthouse, Michael B.

AU - Abdul Malik, K. M.

PY - 2000/1/1

Y1 - 2000/1/1

N2 - Reaction of 3-cyanochromone with methylenetriphenylphosphorane yields the stabilised ylide (4) by way of a conjugate addition and subsequent ring opening. Variable temperature 1H 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.

AB - Reaction of 3-cyanochromone with methylenetriphenylphosphorane yields the stabilised ylide (4) by way of a conjugate addition and subsequent ring opening. Variable temperature 1H 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.

KW - 3-cyanochromone

KW - Conjugate addition

KW - Methylenetriphenylphosphorane

KW - Variable temperature H NMR spectroscopy

KW - X-ray crystallography

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DO - 10.1080/10426500008076534

M3 - Article

AN - SCOPUS:0034366297

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JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

SN - 1042-6507

IS - 1

ER -

Conjugate addition of a phosphorus ylide to 3-cyanochromone

Abstract

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