“…and 2-(decylperoxy)tetrahydro-2 H -pyran ( 13a , 1.00 equiv, 129.2 mg, 500. μmol) to provide no ketene N , O -acetal but, rather, 7-butyl-6-nitro-1-methylindole as a dark-brown oil, following isolation (35.9 mg, 31%). This product, formed by undesired nucleophilic aromatic substitution of n -BuLi, matched the predictions laid forth by previous groups . Characterization: R f = 0.32 (5% EtOAc/Hex); 1 H NMR (600 MHz, CDCl 3 ): δ 7.57 (d, J = 8.69 Hz, 1H), 7.48 (d, J = 8.69 Hz, 1H), 7.19 (d, J = 3.02 Hz, 1H), 6.53 (d, J = 3.02 Hz, 1H), 4.11 (s, 3H), 3.23 (t, J = 8.30 Hz, 2H), 1.85–1.77 (tt, J = 7.54, 7.54 Hz, 2H), 1.59–1.51 (tq, J = 7.54, 7.55 Hz, 2H), 1.02 (t, J = 7.55 Hz, 3H); 13 C{ 1 H} NMR (150 MHz, CDCl 3 ): δ 145.6, 135.8, 133.8, 133.0, 123.1, 118.9, 116.6, 101.8, 37.5, 34.6, 26.9, 22.9, 13.9.…”