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. Author manuscript; available in PMC: 2014 Dec 31.
Published in final edited form as: Nat Chem. 2013 Nov 17;6(1):34–40. doi: 10.1038/nchem.1797

Figure 4. Studies giving insight to a) the importance of reaction conditions and b/c) the mechanism of the HDDA//aromatic ene reactions.

Figure 4

a, Attempted aromatic ene reaction of the aryne 34 generated by elimination of HBr from the aryl bromide 33 shows an advantage of use of the reagent-free conditions of the HDDA reaction as the method for aryne formation. b, A pair of complementary deuterium-labeling experiments strongly implicate the intermediacy of the isotoluene 39. c, The cis-addition of carbon and deuterium across the maleic anhydride π-bond (see Supplementary Information for a discussion of the 1H NMR-based assignment of the structure 41-d3) provides strong mechanistic evidence for the concerted nature of the bimolecular (Alder) ene reaction.