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Reagents: i, CH,=CHCOMe, benzene, 17,4 d; ii, DDQ, benzene, tl, 4 d. ~~ With but-3-en-2-one, 2-isopropenylbenzofuran (124, Scheme 31) affords the adducts 126 and 127 in a combined yield of 29%. When the crude product was dehydrogenated with 2,3-dichloro-5,6-dicyano1,Cbenzoquinone in boiling benzene, the aromatized product 128 (6%) was obtained. It was accompanied by the dicyanodibenzofuran 129, which was found to arise from the excess diene present in the reaction mixture. '30 2-Isopropenylbenzofuran (124), on reaction with dimethyl acetylenedicarboxylate, affords the dibenzofuran 130 (Scheme 32), the intermediate dihydrodibenzofuran undergoing dehydrogenation at the expense of the diene in as much as some 2-isopropylbenzofuran was isolated.

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The resultant adduct 96 on boiling with molar aqueous sodium hydroxide yields the tetrahydro-2-dibenzofuranone 97. ' 2 1 (97) (96) SCHEME 24 The 3(2H)-benzofuranone 98 undergoes Michael addition with (E)-pent3-en-2-one (100, Scheme 25) in the presence of sodium ethoxide to afford the adduct 101 as a mixture of two racemates. Cyclization to the 2-dibenzofuranone 102 can be induced by boiling with dilute aqueous sodium hydroxide under nitrogen or to the aromatized compound 103 in the presence of air.

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