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. Author manuscript; available in PMC: 2011 Dec 17.
Published in final edited form as: J Org Chem. 2010 Nov 16;75(24):8392–8399. doi: 10.1021/jo101505x

Table I.

Summary of Rate Studies for the Et2NLi-Mediated Reactions (eqs 2 and 3)

Entry Substrate Product(s) THF order Et2NLi
order		 kH/kDd kH/kDe
1 1 2+3 2.0 ± 0.1a 0.54 ± 0.03b 1.1 ± 0.1 1.22 ± 0.05
2 2 2.0 ± 0.1a 0.52 ± 0.03b 1.1 ± 0.1 1.12 ± 0.05
3 3 2.5 ± 0.1a 0.57 ± 0.03b 1.1 ± 0.1 3.02 ± 0.04
4 4 5+7 0a 0.98 ± 0.05c
5 5 0a 0.99 ± 0.04c
6 7 1.29 ± 0.05a 0.59 ± 0.04c
a

[Et2NLi] = 0.10 M.

b

[THF] = 3.9 M in toluene cosolvent.

c

[THF] = 6.0 M in toluene cosolvent.

d

Measured using 1 and 1,1-1-d2.

e

Measured using 1 and 2,2-1-d2.