Additions to and Substitutions at C-C &pgr;-Bonds, Volume 4 by M.F. Semmelhack

By M.F. Semmelhack

Quantity four specializes in additions and the ensuing substitutions at carbon-carbon &pgr;-bonds. half 1 comprises procedures in general regarded as easy polar reactions, reactive electrophiles and nucleophiles including to alkenes and alkynes. a big subject is Michael-type addition to electron poor &pgr;-bonds, featured within the first six chapters. partially 2 are accrued the 4 basic methods resulting in nucleophilic fragrant substitution, together with radical chain strategies and transition steel activation via to &pgr;-complexation. Metal-activated addition (generally by way of nucleophiles) to alkenes and polyenes is gifted partly three, together with allylic alkylation catalyzed by way of palladium. The insurance of nonpolar additions partially four contains radical additions, organometal addition (Heck reaction), carbene addition, and 1,3-dipolar cycloadditions.

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Extra resources for Additions to and Substitutions at C-C &pgr;-Bonds, Volume 4

Example text

When the orbitals undergoing the change lie on the same face of the molecules which are reacting (called suprafacial way). or 2. When the overlap of the reacting orbitals or product orbitals occurs on the opposite faces of the reacting molecules (called antarafacial way). (+ ) (+ ) (+) (+ ) (–) (–) (–) (–) S u pra fa cial a ttack A n tara fa cial atta ck Bonding π orbital overlap of ethene with atomic S orbital. Fig. 1 The same definitions apply to longer π systems Suprafacial use of a σ bond involves bonding in the same way at both terminals.

When the orbitals undergoing the change lie on the same face of the molecules which are reacting (called suprafacial way). or 2. When the overlap of the reacting orbitals or product orbitals occurs on the opposite faces of the reacting molecules (called antarafacial way). (+ ) (+ ) (+) (+ ) (–) (–) (–) (–) S u pra fa cial a ttack A n tara fa cial atta ck Bonding π orbital overlap of ethene with atomic S orbital. Fig. 1 The same definitions apply to longer π systems Suprafacial use of a σ bond involves bonding in the same way at both terminals.

C C (+ ) (–) (+) (– ) C C (–) (–) L U M O (gro un d state) H O M O (e xcited state) Th e photoche m ical com bina tion Fig. 6 The flanking groups from the same lobe (suprafacially) or from opposite lobes (antarafacially). 36 MECHANISMS IN ADVANCED ORGANIC CHEMISTRY S u pra fa cial A n tara fa cial Fig. 6 The symbols π, σ and ω are given respectively to the π systems, σ bonds and lone p orbitals which participate in the transition state and the symbols (s) and (a) are indicated for their suprafacial and antarafacial use.

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