Stereoelectronic Effects

Spiroketal Formation


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Spiroketal formation

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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.