Stereoelectronic Effects Spiroketal Formation

Spiroketal formation

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

The usual mechanism for acetal formation is followed and initially the spiroketal forms the axial-equatorial (ax-eq) conformation which equilibrates to the more stable chair-chair axial-axial (ax-ax) conformation.

Energy Profile Diagram for the Equilibration

J. E. Aho, P. M. Pihko and T. K. Rissa, Chem. Rev., 2005, 105, 4406–4440.

F. Perron and K. F. Albizati, Chem. Rev., 1989, 89, 1617–1661.

 

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