Synthetic equivalents to substituted acetylenes in cycloaddition reactions. Dienophilic reactivity of 2-methyl-, 2-phenyl- and 2,3-trimethylene-1,4-benzodithiins-1,4-tetroxides

Add time:09/08/2019    Source:sciencedirect.com

Dienophiles 2-methyl-1,4-benzodithiin-1,4-tetroxide (3a), 2-phenyl-1,4-benzodithiin-1,4-tetroxide (3b) and 2,3-trimethylene-1,4-benzodithiin-1,4-tetroxide (3c) have been prepared with different methods starting from benzene-1,2-dithiol (1). Their reactivity was tested towards cyclopentadiene, sulfolene, furan and 1,3-cyclohexadiene. The Diels-Alder adducts to cyclopentadiene were converted into the corresponding unsaturated hydrocarbons, mimicking the Diels-Alder reaction of substituted acetylenes. The X-ray structure determinations of 4b, a secondary product in the preparation of 2-phenyl-1,4-benzodithiin-1,4-tetroxide and of the adduct of the phenyl substituted derivative with cyclopentadiene 8b are reported.

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