Abstract
Abstract The photochemical reaction of 3,3-dimethyl-1,2-indanedione (DMID) with xanthene was investigated in detail. The products are 1-hydroxy-3,3-dimethyl-1-(9-xanthenyl)-2-indanone (3a) (49%), 2-hydroxy-3,3-dimethyl-1-indanone (13%), 1,1′-dihydroxy-3,3,3′,3′-tetramethyl-1,1′-biindan-2,2′-dione (5a) (23%), and 9,9′-bixanthenyl (6) (49%). The reaction proceeds via hydrogen abstraction by 3(nπ)* of DMID leading to triplet radical pair composed of its semidione radical and 9-xanthenyl radical. The product 3a is a combination product from the radical pair, while 5a and 6 are escaping products from it. The hydrogen abstraction occurs at C-1 carbonyl group of DMID in a fairly efficient quantum yield (Φ=0.71). Behavior of the DMID semidione radical is rather resemble those of open-chain semidione radicals than those of sterically hindered semidione radicals.
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