Abstract
AbstractDiels–Alder cycloaddition reactions of 1,3,5‐hexatriynes with tetraphenylcyclopentadienone have been performed, and mainly gave 1,2‐diethynyl‐3,4,5,6‐tetraphenylbenzene derivatives as products. The Diels–Alder reactions were optimized under conventional heating and microwave irradiation conditions, and showed good selectivity towards the central carbon–carbon triple bond of the triyne. Empirical evidence suggests that the selectivity of the reaction is governed predominantly by the steric demands of the end‐groups of the triyne. Several of the Diels–Alder products could be further elaborated by a sequence of desilylation and oxidative homocoupling to provide dimeric products. The homocoupling reaction was optimized by Pd catalysis. The X‐ray crystallographic analysis of two derivatives is reported.
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