Cycloaddition of 2,3-dimethyl-1,3-butadiene to 1,4-benzoquinonemonoimine derivatives
Abstract
N-Arylsulfonyl-1,4-benzoquinonemonoimines add 2,3-dimethyl-1,3-butadiene to free С5=С6 bond of quinoid ring with formation of N-(6,7-dimethyl-4-oxo-4a,5,8,8a-tetrahydronaphthalen-1(4H)-ilyden)-4-methylbenzenesulfonamides which in the acid medium convert to tautomeric N-(4-hydroxy-6,7-dimethyl-5,8-dihydronaphthalen-1-yl) arylsulfonamides. N-Phenoxy(benzilyden)acetyl-2,3-dimethyl-1,4- benzoquinonemonoimines add 2,3-dimethyl-1,3-butadiene to alkylsubstituted С2=С3 bond of quinoid ring with formation of N-(4a,6,7,8a-tetramethyl-4-oxo-4,4a-dihydronaphthalen-1(8aH)-ylidene)acylamides.
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