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Suprafacial -rearrangement of cyclopentadiene C

The orbitals on both sides of the correspondence diagram are [2 x a -h a ] and the rearrangement via the suprafacial transition state in clearly allowed in agreement with both the Woodward-Hoffmann Rules and experiment. It is [Pg.203]

The alternative choice would exchange the symmetry labels of the two anasymmetrized tt orbitals, but the electron configuration would remain the same. [Pg.203]

The strongest presumptive evidence for facile sigmatropic shifts that obey the Woodward-Hoffmann Rules is cited for molecules with a cyclic a frame in which the migrating bond is to carbon rather than to hydrogen [30, pp. 98-103]. A particularly intriguing example, discovered by Berson and Wilcott some 25 years ago [40], is illustrated in Fig. 8.10. [Pg.204]




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