Derivate des Benzo[1.3]dioxols, 44 [1] Darstellung von p-chinoiden Brenzkatechinmethylenethern

F r a n z D a l l a c k e r * , G e r m a n u s R e i c h r a t h u n d G e r a r d S c h n a c k e r s Institut für Organische Chemie der Technischen Hochschule Aachen, Prof.-Pirlet-Straße 1, D-5100 Aachen Z. Naturforsch. 34b, 624-632 (1979); eingegangen am 13. November 1978 5,6-Dimethyl-l,3-benzodioxole-4,7-quinone, 6,7-Dimethyl-l,4-benzodioxan-5,8-quinone, 7,8 -Dimethyl 3,4 -dihy dro 2 H -1,5 -benzodioxepin 6,9 -quinone, 8.9-Dimethyl-2,3,4,5-tetrahydro-l,6-benzodioxocin-7,10-quinone, 9.10-Dimethyl-3,4,5,6-tetrahydro-2H-l,7-benzodioxonin-8,l 1-quinone The preparation of 5,6-dimethyl(lg), 5-methoxy-6-methyl-l,3-benzodioxole-4,7quinone(lk), 6,7-dimethyl-l,4-benzodioxan-5,8-quinone (3e), 7,8-dimethyl-3,4-dihydro2H-l,5-benzodioxepin-6,9-quinone (4e), 8,9-dimethyl-2,3,4,5-tetrahydro-l,6-benzodioxocin-7,10-quinone (5f) and of 9,10-dimethyl-3,4,5,6-tetrahydro-2H-l,7-benzodioxonin8.11-quinone (6e) by potassiumnitrosodisulfonate-oxidation of the phenols lf, lj , 3d, 4d, 5e, and 6d is described. To obtain the phenols by Baeyer-Villigeroxidation of the aldehydes le, l i , 3c, 4c, 5d, 6c, the cyclic ethers are subjected to bromination, brominelithium-exchange, and formylation of the lithium-compounds.