Spiroketal Formation – Stereoelectronic Effects

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.

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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