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. 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 2.

Summary of Rate Studies for the Anionic Snieckus-Fries Rearrangement

ArLi Solvent R X Temperature °C LDA Order Solvent Order
7a THF Me F -40 0
-0.48±0.04		 +1.08±0.05a
+2.4±0.6b
7d n-BuOMe Et OMe 15 0c
+0.49±0.09d 		0
-1.10±0.05
6be HMPA Et OMe -65 0 +0.8±0.1
6de HMPA Me F -78 0 +1.2±0.3
7e DME Me F -60 0 0
6g TMCDA Et OMe -25 0 0
a

0.42 M LDA.

b

0.098 M LDA.

c

7.0 M n-BuOMe.

d

1.3 M n-BuOMe.

e

The order in THF cosolvent is zero.