Organophosphorus chemistry 32. 1 The reaction of vanillin, ortho-vanillin and piperonal with stabilized methylenetriphenylphosphoranes (wittig reagents)

Article abstract of DOI:10.1080/10426509808045482

Vanillin (1) and piperonal (3) reacted with ylidenetriphenylphosphoranes 4a-f in boiling toluene following the Wittig mechanism to give the ethylenes 5a-f and 7a-f. Similarly, ethylenes 8c-f were produced when ortho-vanillin (2) was allowed to react with 4c-f. The reaction of aldehyde (2) with the P-ylides 4a,b yielded the Wittig products 8a,b and 8-methoxycoumarin (10). Triphenylphosphine oxide (TPPO, 6) was isolated and identified in all cases. The mechanism for formation of 10 was discussed. Structural reasonings for all new compounds were based upon compatible elementary as well as spectroscopic (IR, ¹H-NMR and MS) measurements.

Full text of DOI:10.1080/10426509808045482

Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: http://www.tandfonline.com/loi/gpss20
ORGANOPHOSPHORUS CHEMISTRY 32.
THE REACTION OF VANILLIN, ORTHO-
VANILLIN AND PIPERONAL WITH STABILIZED
METHYLENETRIPHENYLPHOSPHORANES (WITTIG
REAGENTS)
Taghrid S. Hafez , Maged M. Henary , Mohamed Refat & H. Mahran
To cite this article: Taghrid S. Hafez , Maged M. Henary , Mohamed Refat & H. Mahran (1998)
ORGANOPHOSPHORUS CHEMISTRY 32. THE REACTION OF VANILLIN, ORTHO-VANILLIN
AND PIPERONAL WITH STABILIZED METHYLENETRIPHENYLPHOSPHORANES (WITTIG
REAGENTS), Phosphorus, Sulfur, and Silicon and the Related Elements, 143:1, 33-44, DOI:
10.1080/10426509808045482
To link to this article: http://dx.doi.org/10.1080/10426509808045482
Published online: 04 Oct 2006.
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Date: 02 March 2016, At: 23:46