Cycloaddition of ( E )- N -[2-([2.2]paracyclophan-4-yl)ethylidene] methylamine- N -oxide with 2,3-diphenylcyclopropenones and dibenzoyl acetylene;synthesis of new paracyclophanylpyrroles
Free accessResearch articleFirst published online August, 2007
Cycloaddition of ( E )- N -[2-([2.2]paracyclophan-4-yl)ethylidene] methylamine- N -oxide with 2,3-diphenylcyclopropenones and dibenzoyl acetylene;synthesis of new paracyclophanylpyrroles
When N-[2-([2.2]paracyclophan-4-yl)ethylidene]methylamine-N-oxide (1) is treated with cyclopropenones 6a–c, the [2.2]paracyclophane-based pyrrole(-2-one, -thione and -ylidene malnonitrile) 7a–c are formed in good yields via formal [3π + 3π]cycloaddition. The reaction of 1 with dibenzoyl acetylene (12) afforded, via a Michael-type reaction, the stereoisomeric pyrrole 13. The reaction mechanism described the products formation is discussed.
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