ACTION OF WITTIG-HORNER REAGENTS ON ORTHO-QUINONES

When 3, 4, 5, 6-tetrachloro-l, 2-benzoquinone (1) was reacted with two molar amounts of triethylphosphonoacetate (I), the corresponding 5, 6, 7, 8-tetrachlorocoumarin-4-carbethoxy-3-diethylphosphonate (4) was obtained. Moreover, phenanthrene-9, 10-quinone (2) was converted by reaction of Wittig-Horner reagent (I) into 2, 3-dicarbethoxy-phenanthro[9, 10-b]dihydrofuran (5) and the dimeric form (6). On the other hand, adducts (7) and (8) were isolated from the reaction of acenaphthenequinone (3) with triethylphosphonoacetate (I). Possible reaction mechanisms are considered and the structure of the new compounds (4), (5, 6) and (7, 8) was confirmed on the basis of the elemental analysis and spectral studies. © 1992, Taylor & Francis Group, LLC. All rights reserved.