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Pericyclic Reactions (McM chapt 30)

Pericyclic Reactions (McM chapt 30). Polar react. (nucleophiles and electrophiles) Radical react. Pericyclic react. (concerted, cyclic TS # ) Electrocyclic react. Cycloadditions (i.e. Diels Alder) Sigmatropic rearrangement. Rearrangement of polyene Termal (react. in ground state)

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Pericyclic Reactions (McM chapt 30)

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  1. Pericyclic Reactions (McM chapt 30) • Polar react. (nucleophiles and electrophiles) • Radical react. • Pericyclic react. (concerted, cyclic TS#) • Electrocyclic react. • Cycloadditions (i.e. Diels Alder) • Sigmatropic rearrangement • Rearrangement of polyene • Termal (react. in ground state) • or photochemical • (react of exited state)

  2. Symmetry Allowed React. Woodward Hoffmann rules Symmetry in reactants are preserved during pericyclic react. Results can generally be predicted just by looking at Front Orbitals (FMO; HOMO and LUMO) - Fukui

  3. Molecular orbitals 1,3-butadiene Stereospesific react. S: Symmetric A: Antisym.

  4. Molecular orbitals hexatriene Symmetry allowed react

  5. Photochemical electrocyclic react.

  6. Cycloadditions (i.e. Diels Alder) Stereospesific react.

  7. endo - exo selectivity Normal electron demand DA - Electron poor dienophile (Michael accept.) Ethene etc, very low react. Michael accept. Lower LUMO

  8. [2+2] Cycloadditions

  9. Carbene Cycloadditions

  10. Sigmatropic Rearrangements [3,3] Rearrangements; Claisen rearrang. etc.

  11. [1,5] Rearrangement (H-shift) [1,3] Rearrangement (H-shift)

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