. Author manuscript; available in PMC: 2009 Oct 15.

Published in final edited form as: J Am Chem Soc. 2008 Sep 18;130(41):13709–13717. doi: 10.1021/ja804087r

Table 1.

⁶Li and ¹⁵N NMR spectroscopic data^a,^b

ArLi	Solvent	R	X	⁶Li, δ (mult,¹J_LiN	¹⁵N, δ(mult)
6a^c	THF	i-Pr	F	1.23 (s)	--
6c^b	HMPA	i-Pr	OMe	0.91 (s)	--
6e	HMPA	i-Pr	F	0.75 (s)	--
6f^c,^b	DME	i-Pr	F	1.65 (s)	--
6g^b	TMCDA	Et	OMe	2.18 (s)	--
7b^b	THF	i-Pr	F	1.71 (d, 5.3)	76.3 (q)
7d^b	n-BuOMe	Et	OMe	1.85 (d, 5.8)	75.8 (q)
7f^b	DME	i-Pr	F	1.60 (d, 5.4)	75.2 (q)
7g	TMEDA	i-Pr	OMe	2.01 (d, 4.9)	75.3 (q)
7h	Me₂NEt	Et	OMe	1.93 (d,5.2)	75.3 (q)
8a	TMEDA	i-Pr	OMe	0.78 (d, 5.7) 2.49 (t, 4.7) 2.50 (d, 5.7)	73.8 (tt) 75.3 (q)
8b	Me₂NEt	Et	OMe	0.81 (d, 6.3) 2.24 (d, 6.0) 2.80 (t, 4.9)	74.2 (tt) 74.3 (q)
9a	THF	Me	F	0.40 (d, 4.8)	79.1 (q)
9b	n-BuOMe	Et	OMe	0.93 (d, 4.9)	75.1 (q)
9c	HMPA	Et	OMe	0.54 (d, 5.3)	76.5 (q)
9d	HMPA	Me	F	0.66 (d, 4.6)	76.3 (q)
10a	n-BuOMe	Et	OMe	1.49 (d, 5.5) 1.55 (d, 6.2) 1.89 (t, 5.2)	74.4 (--)^d 74.1 (--)^d
10b	HMPA	Et	OMe	1.09 (d, 5.3) 1.12 (d, 5.3) 1.58 (t, 4.6)	73.2 (--)^d 74.7 (tt)
10c	DME	Me	F	0.95 (d, 4.7) 0.98 (d, 5.1) 1.82 (t, 5.1)	72.9 (q) 74.3 (q)
10d	TMEDA	Me	OMe	1.21 (d, 5.0) 1.67 (t, 4.9)	74.9 (q) 75.1 (q)
10e	Me₂NEt	Et	OMe	1.79 (d, 6.2) 1.79 (t, 5.1) 1.84 (d, 6.1)	73.8 (tt) 74.3 (tt)

Multiplicities are denoted as follows: s, singlet; d, doublet; t, triplet; q, quintet. The chemical shifts are reported relative to 0.30 M ⁶LiCl/MeOH (δ 0.0 ppm) and neat Me₂NEt (δ 25.7 ppm) at -90 °C. ¹³C NMR spectra are referenced to toluene-d₈ (δ 137.9 ppm), pentane (δ 14.1 ppm), or THF (δ 67.6 ppm). Chemical shifts are reported in ppm, and J values are reported in Hz.

Carbon-13 resonances of the carbanionic carbons: 6c, δ 158.7 (br s); 6f, δ 150.1 (br d, J_FC=7.7); 6g, δ 155.1 (t, J_CLi=120.7); 7b, δ 150.5 (br d, J_FC=123); 7d, δ 155.2 (q, J_CLi=5.7); 7f, δ 154.6 (dq, J_FC=123, J_CLi=5.9).

1.0 equiv [⁶Li,¹⁵N]LDA.

Obscured by another resonance.