REACTIONS OF 2,2'5'2''-TERFURAN

Formylation of 2,2',5',2 ''-terfuran (1) with N-methylformanilide and phosphorus oxychloride gave 5-formyl-2,2',5',2 ''-terfuran (2) and 5,5 ''-diformyl-2,2'5',2 ''-terfuran (3). Reduction of 2 and 3 afforded 5 -hydroxymethyl-2,2',5',2 ''-terfuran (4) and 5,5 '' dihydroxymethyl-2, 2',5', 2 ''-terfuran (5), respectively. Terfuran 1 reacted with phenyl magnesium bromide to give 5-(phenylhydroxymethyl)-2,2',5',2 ''-terfura n (6), and was carbonated to 5-carboxy 2,2',5',2 ''-terfuran (7) and 5 ,5 ''-dicarboxy-2,2',5',2 ''-terfuran (8). Bromination of 1 with N-bro mosuccinimide gave 5,5 ''-dibromo 2,2',5',2 ''-terfuran (9).