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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 5.

Phosphine Substituent Effects on Rearrangement.

graphic file with name nihms424873t6.jpg
Entry R Yielda kf+rb kfb Keq ΔGexpc
29a 29b Cy 72% - - -d -
11a 11b t-Bu 59% 1.00 ± 0.03 1.00 ± 0.03 8.71 ± 0.15 −1.26 ± 0.01
30a 30b Ad 37% 0.87 ± 0.04 0.87 ± 0.03 9.00 ± 0.16 −1.28 ± 0.01
a

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

b

Relative to 11a in THF-d8.

c

In kcal/mol.

d

Rearranged product not observed. Ad = adamantyl