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Antarafacial




Many Sigmatropic Reaction s and Cycloaddition s can be either suprafacial or antarafacial and this determines the Stereochemistry .

An example is the shift in which the interacting Frontier Orbital s are the Allyl Free Radical and the Hydrogen 1s orbitals. The suprafacial shift is Symmetry Forbidden because orbitals with opposite algebraic signs overlap. The symmetry allowed antarafacial shift would require a Strained Transition State and is also unlikely. In contrast a symmetry allowed and suprafacial [1,5 -hydride shift is a common event F.A. Carey, R.J. Sundberg, ''Advanced Organic Chemistry'' Part A ISBN 0-306-41087-7.

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