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. Author manuscript; available in PMC: 2014 Sep 26.
Published in final edited form as: Org Lett. 2010 Jan 1;12(1):96–99. doi: 10.1021/ol902415s

Table 2.

ΔG‡ Values in kcal/mol for the Reaction of Indolynes with Substituted Furans

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entry aryne furan, R ΔG‡ (a) ΔG‡ (b)
1 21 H 10.5
2 22 H 10.0
3 23 H 8.7 (8.4)a
4 21 t-Bu 6.3 7.3
5 22 t-Bu 6.9 6.1
6 23 t-Bu 7.0 (8.0) b
7 23 Me 9.2 (9.4) 7.5 (7.8)
8 23 Et 9.0 (9.4) 7.8 (8.2)
9 23 i-Pr 9.7 (10.3) 7.6 (8.2)
a

Values in parentheses include continuum ethereal solvation effects.

b

No barrier to reaction is predicted in the gas phase or continuum solution.