Organic letters

Formal [(2+ 2)+ 2] and [(2+ 2)+(2+ 2)] Nonconjugated Dienediyne Cascade Cycloadditions

YT Wu, A Linden, JS Siegel

Index: Wu, Yao-Ting; Linden, Anthony; Siegel, Jay S. Organic Letters, 2005 , vol. 7, # 20 p. 4353 - 4355

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Citation Number: 15

Abstract

Through-space interaction between proximal olefins, as in norbornadiene (NBD), leads to reactivity analogous with conjugated dienes. 1 NBD reacts directly with tetracyanoethylene to give a homo-Diels−Alder [(2+2)+2] adduct. 2 In the presence of transition-metal catalysts, NBD and acetylenes generate homo-Diels−Alder products among other coupling products, depending on the catalyst. 3 Similar perturbations of reactivity could be anticipated for functional ...