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. Author manuscript; available in PMC: 2009 Nov 7.
Published in final edited form as: J Org Chem. 2008 Oct 9;73(21):8175–8181. doi: 10.1021/jo800923a

Table 3.

UB3LYP/6–31G(d) calculated free energies (relative to radical a) for rearrangements of siloxycycle substituted cyclohexyl radicals to cyclopentylmethyl radicals.

graphic file with name nihms91073t3.jpg
compound Substituents TS1 Radical b TS2 Radical c
19-eq R3 = H, R4 = CH=CH2 16.8 −2.3 8.7 −4.3
20-eq R3 = OH, R4 = CH=CH2 14.5 −7.6 6.6 −4.0
21-eq R3 = H, R4 = (E)CH=CH-CH=CH2 12.4 −6.7 2.3 −6.1
22-eq R3 = OH, R4 = (E)CH=CH-CH=CH2 11.1 −11.0 1.6 −11.0