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Download e-book for kindle: Arene chemistry : reaction mechanisms and methods for by Jacques Mortier

By Jacques Mortier

ISBN-10: 1118752015

ISBN-13: 9781118752012

ISBN-10: 1118754956

ISBN-13: 9781118754955

ISBN-10: 1118754980

ISBN-13: 9781118754986

Geared up to let scholars and artificial chemists to appreciate and extend on fragrant reactions coated in origin classes, the e-book deals a radical and available mechanistic clarification of fragrant reactions concerning arene compounds.

•    Surveys tools used for getting ready arene compounds and their transformations
•    Connects reactivity and technique with mechanism
•    Helps readers observe fragrant reactions in a pragmatic context by way of designing syntheses
•    Provides crucial information regarding concepts used to figure out response mechanisms

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Extra resources for Arene chemistry : reaction mechanisms and methods for aromatic compounds

Example text

Other approaches of evaluating electrophile strengths have been developed, including ­comparisons of the regioselectivities of electrophilic attacks. The assumption is that more ­reactive electrophiles should exhibit less positional selectivity in chemistry with substituted arenes. In a method developed by Brown and associates [21], electrophiles were compared by the relative reactivities of the meta and para positions of toluene, where more reactive electrophiles give increasing proportions of meta substitution.

This was evident from measurement of the α‐bond angles and C1─Si bond lengths. Similar trends were observed in recent computational study that examined the potential energy surface for the Friedel–Crafts alkylation of benzene [45]. The MP2/6‐31+G**(fc) calculations studied the reactions of benzene with the methyl cation, the isopropyl cation, and the tert‐butyl cation. 6). Both the η1 and η2 hapticity π‐complex structures were found to be comparable in energy and about 10 kcal/mol more stable than the gas‐phase starting materials.

1 Examples of electrophiles formed by direct protonation. 2 Electrophiles generated from Brønsted acids. There are many examples of Brønsted acid‐promoted reactions where highly polarized functional groups are the active electrophiles. For example, Olah and coworkers reported N‐ c­hlorosuccinimide to be a powerful chlorinating agent with superacidic BF3─H2O [11]. The active electrophile is likely the diprotonated (14) or triprotonated species (15, Eq. 3) Cl 7 ELECTROPHILES which t­ransfers Cl+ directly to the arene nucleophile.

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Arene chemistry : reaction mechanisms and methods for aromatic compounds by Jacques Mortier


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