Abnormal triynes, in which a carbonyl group is activating the diyne instead of the monoyne subunit, revealed an interesting behavior with furan. In competition with cyclization in an HDDA fashion to produce 2, the central alkyne moiety in substrate 1, activated by both a carbonyl group and another alkyne, reacts bimolecularly with furan. The resulting intermediate further undergoes a [2+2+2] cyclization to give the multi-cyclic compound 3. Mechanistic, computational, and structural aspects will be presented.

Abnormal substrates give “abnormal” products: Competition between classical Diels–Alder vs. hexadehydro-Diels–Alder (HDDA) reactions

249th National Meeting (2015)

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