Diels-Alder reactions of anthracenes with C-sulfonyldithioformates

• C-Sulfonyldithioformates (2) (R-1 = ArSO2, R 2 = ArS) readily add to anthracene and 9-methylanthracene (1) in a Diels-Alder fashion with formation of 9,10-dihydro-10,9-(epithiomethano)anthracenes (3) which in turn may suffer thermally induced elimination of arenesulfinic acid to yield the 9-anthracenedithiocarboxylic esters (4). The reactions with the unsymmetrical diene 9-methylanthracene take place in a highly stereoselective fashion.

Nyckelord

thiocarbonyl compounds

s-oxide

generation

sulfoxide

<4+2>-cycloadditions

thioaldehydes

thioketones

thermolysis

reactivity

sulfines

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