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. Author manuscript; available in PMC: 2013 Dec 5.
Published in final edited form as: J Am Chem Soc. 2012 Nov 27;134(48):19922–19934. doi: 10.1021/ja310351e

Table 4.

Halide Effects on Rearrangement.

graphic file with name nihms424873t5.jpg
Entry Kf+rc kfc Keq ΔGexp (kcal/mol)
26a 26b 2.84 ± 0.08 2.18 ± 0.07 2.15 ± 0.04 −0.44 ± 0.01
11a 11b 1.00 ± 0.03 1.00 ± 0.03 8.71 ± 0.15 −1.26 ± 0.01
28a 28b -d -d 0.04e 1.87 ± 0.01
a

Isolated yield, prepared in the same manner as in Table 2.

b

Decomposed in solution.

c

Relative to 11a in THF-d8.

d

Kinetics unreliable due to small change in [28a] over time.

e

Value in C6D6, estimated error is less than ± 0.01.