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. Author manuscript; available in PMC: 2012 May 25.
Published in final edited form as: J Am Chem Soc. 2011 May 3;133(20):7916–7925. doi: 10.1021/ja201249c

Figure 8.

Figure 8

Fractional-order catalysis by methanol in the epoxide-opening spirocyclization a substrate lacking the glycal ring oxygen. a) Methanol-catalyzed epoxide-opening spirocyclization of cyclohexene oxide 27 with inversion of configuration to afford spiroether 28. b) Plot of kobs (min−1) for spiroether formation at varying [CD3OD] yields a fractional-order curve. Mean values over two replicate experiments shown. c) Plot of kobs (min−1) versus [CD3OD]0.59 yields a linear correlation, consistent with the fractional-order dependence on methanol. Mean values over two replicate experiments shown.