Abstract
Thiobenzophenone and its 4,4′-dicholro derivative combine as dienes (C S + aromatic CC bond) with dimethyl acetylenedicarboxylate, methyl propiolate, dicyanoacetylene, and cyclooctyne furnishing 1 H-2-benzothiophyrans 10, 11, 13, 14; the primary [4 + 2] cycloaddition is followed by 1,3-prototropy. In the case of the strained ( E)-cyclooctene as a dienophile, the initial nonaromatic cycloadducts 19 were isolated and rearomatized by base catalysis. - In the MS of the 1 H-2-benzothiopyrans, M + and [M + - are preeminent, both as a results of benzylic cleavage. R H, Cl; R 1CCR 1 = dimethyl acetylenedicarboxylate, dicyanoacetylene, cyclooctyne. With trans-cyclooctene as a dienophile, the initial nonaromatic adduct is isolable.
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