Arenes => alkenes

Trifluoromethyl groups that are bound to sp2 carbons of alkenes, arenes, or heterocyclic compounds are slightly deshielded compared to the saturated counterparts, but the influence is relatively small (Scheme 5.32). 

Fig. 32 Examples of Wagnerova Type II photooxygenations of alkene, arene, and alkane substrates.

Cationic Group 11 carbonyl complexes have been implicated in catalytic carbony-lation reactions of alkenes, arenes, alcohols, saturated hydrocarbons and aldehydes under acidic conditions [106]. While the mono- and di-carbonyls [M(CO)] and [M(C0)2] (M = Cu, Ag, Au) can be formed at atmospheric pressure of CO, only Cu(I) forms a tricarbonyl cation under such conditions [107]. Strauss and co-workers reported the observation of [Ag(CO)3] when a Fluorolube mull of Ag[Nb(OTep5)5] was subjected to 13 bar CO in an HP IR transmission cell [108]. 

The first chapter concerns the chemistry of the oxidation catalysts, some 250 of these, arranged in decreasing order of the metal oxidation state (VIII) to (0). Preparations, structural and spectroscopic characteristics are briefly described, followed by a summary of their catalytic oxidation properties for organic substrates, with a brief appendix on practical matters with four important oxidants. The subsequent four chapters concentrate on oxidations of specific organic groups, first for alcohols, then alkenes, arenes, alkynes, alkanes, amines and other substrates with hetero atoms. Frequent cross-references between the five chapters are provided. 

Unfortunately there is no simple correlation between gas-phase ionization potentials and solution-phase oxidation potentials for all classes of compounds, because the energy of solvation is highly dependent on molecular structure. Nevertheless, for closely related compounds there tends to be a linear correlation between ionization potentials in the gas phase and in solution [76, 77]. The air-sensitivity of electron-rich alkenes, arenes, or heteroarenes can therefore be estimated by inspecting either their gas-phase ionization potentials or their oxidation potentials in solution... 

A review which covered the different known methods for the preparation of chiral amines and analysis of the different chiral catalysts used, correlating them according to their efficiency, selectivity, and flexibility, has been presented.279 Reduction reactions of alkenes, arenes, alkynes and allenes resulting in the formation of two or more C-H bonds280 and reduction and addition reactions of alkynes to alkenes to form one or more C=C bonds281 have been reviewed. 

Chappell, D. and Russell, A.T. (2006) From a-cedrene to crinipellin B and onward 25 years of the alkene-arene meta-photocycloaddition reaction in natural product synthesis. Organic tg Biomolecular Chemistry, 4 (24), 4409-4430. 

Boyd, J.W., Greaves, N., Kettle, J., Russell, A.T., and Steed, J.W. (2005) Alkene-Arene meta photocycloadditions with a four-carbon-atom tetheu efficient approach toward the polycyclic ring systems of aphidicolin and stemodinone. Angewandte Chemie, International Edition, 44, 944—946. 

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