The behavior of 4-triphenylmethyl-1,2-benzoquinone towards alkoxycarbonylmethylene(triphenyl)phosphoranes and triphenylphosphine in acetic anhydride

Article abstract of DOI:10.1080/10426509608029634

The reaction of alkoxycarbonylmethylene(triphenyl)phosphoranes (2) with 4-triphenylmethyl-1,2-benzoquinone (1) in acetic anhydride at room temperature for 7 h led to the formation of alkyl (6-acetoxy-α,α,α-triphenyl-m-tolyl)fumarates (7), alkyl (6-acetoxy-α,α,α-triphenyl-m-tolyl)maleates (8), benzofuran derivatives (13 and 14), 3,4-diacetoxytetraphenylmethane (18) along with triphenylphosphine and triphenylphosphine oxide. The action of alcoholic HCl on the fumarates 7 give the coumarin derivatives (19) whereas the maleates 8 yielded 19 and two additional products, alkyl (6-hydroxy-α,α,α-triphenylm-tolyl)maleates (6) and (E)-5-triphenylmethyl-3-alkoxycarbonylmethylenebenzo[b]furan-2(3H)-ones (20). Methylation of the products 6 with methyl iodide in dry acetone and anhydrous potassium carbonate gave the corresponding methyl ethers 21. When the maleates 6 were heated in boiling toluene for about 30 h, a mixture of the coumarin derivatives 19 and (Z)-isomer of 20 was obtained. Triphenylphosphine reacted with quinone 1 in acetic anhydride to give quantitative yield of 18 with triphenylphosphine oxide. Possible reaction mechanisms are considered.

Full text of DOI:10.1080/10426509608029634

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Phosphorus, Sulfur, and Silicon and
the Related Elements
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THE BEHAVIOR OF 4-
TRIPHENYLMETHYL-1,2-
BENZOQUINONE TOWARDS ALKOXY
CARBONYLMETHYLENE(TRIPHENYL)-
PHOSPHORANES AND
TRIPHENYLPHOSPHINE IN ACETIC
ANHYDRIDE
Fayez H. Osman a & Fatma A. El-samahy a
a Department of Pesticide Chemistry , National Research
Center , Dokki, Cairo, 12622, Egypt
Published online: 24 Sep 2006.
To cite this article: Fayez H. Osman & Fatma A. El-samahy (1996) THE BEHAVIOR OF 4-
TRIPHENYLMETHYL-1,2-BENZOQUINONE TOWARDS ALKOXY CARBONYLMETHYLENE(TRIPHENYL)-
PHOSPHORANES AND TRIPHENYLPHOSPHINE IN ACETIC ANHYDRIDE, Phosphorus, Sulfur, and
Silicon and the Related Elements, 108:1-4, 21-30, DOI: 10.1080/10426509608029634
To link to this article: http://dx.doi.org/10.1080/10426509608029634
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