Comprehensive Organic Synthesis: Carbon-Carbon sigma-Bond by Trost B.M., Fleming I., Pattenden G. (eds.)

By Trost B.M., Fleming I., Pattenden G. (eds.)

Quantity three covers carbon-to-carbon unmarried bond forming reactions regarding sp 3, sp 2 and sp carbon facilities, yet purely these which don't contain additions to C-X &pgr;-bonds. the amount first compares and contrasts the alkylation reactions of all kinds of sp 3 carbon nucleophiles and likewise covers vinyl and alkynyl carbanions. Following on from quantity 2, a separate part covers Friedel-Crafts alkylation reactions, that is complemented via discussions of polyene cyclizations and electrophilic transannular cyclizations in synthesis. Coupling reactions resulting in &agr;-bond formation, and concerning every kind of combos of sp 3, sp 2 and sp carbon facilities are subsequent coated, together with these reactions in line with pinacol, acyloin and phenol oxidative coupling reactions, and in addition the Kolbe response. Rearrangement reactions, resulting in carbon-to-carbon &agr;-bond formation, are frequently utilized in a smart demeanour in synthesis. the amount comprises all these rearrangement reactions in keeping with intermediate carbonium ions and carbanions, and likewise contains the benzil-benzilic acid and the Wolff rearrangements. the amount closes with insurance of carbonylation reactions, and using carbene insertion reactions into the C-H bond in synthesis.

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Additional resources for Comprehensive Organic Synthesis: Carbon-Carbon sigma-Bond Formation

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The gas-phase ion chemistry of ionized 1,3,5-cycloheptatriene is closely related to that of ionized toluene, in particular, and to that of norbornadiene and other ‘non-aromatic’ C7 H8 Cž isomers. This extensive body of work will not be discussed here since a detailed review on this topic has been published by one of these authors in the context of the gas-phase chemistry of the alkylbenzene radical cations7,140 . g. C7 H8 Cž . e. the even-electron C7 H9 C ions141 , and alkylcycloheptatrienes, which are closely related to protonated toluene and higher alkylbenzenium ions.

Obviously, formation of antiaromatic cyclopentadienyl cations is circumvented; however, other isomers may also be formed along with the (most stable) arenium-type fragment ions (see below). Open-chain 1,3,5-hexatriene isomers were also found to give similar EI mass spectra. Cyclohexadienes and 1,3,5-Hexatrienes. Not only the standard EI mass spectra but also the CID spectra of the isomeric cyclohexadienes are indistiguishable, as shown by McLafferty and coworkers119 . , C6 H7 C ions, whose structure has been a matter of debate in several aspects (see below)120 – 122 , is preceded by fast hydrogen scrambling.

Ionized 2-phenylbut-2-ene and ionized 1-methylindane, depending on the internal energy of reactants204 . Cooks and coworkers205 studied the reactions of ionized pyrene and the corresponding [M H]C and [M H2 ]Cž ions with neutral isoprene using a quadrupole ion-trap mass spectrometer. Dass206 observed significantly different CID behaviour of the adduct ions formed from neutral 1,3- and 1,4-pentadienes with ionized ketene. Similarly, Bouchoux and Penaud-Berruyer207 found that ion/molecule reactions between ionized vinylamine and twelve neutral C4 , C5 and C6 dienes lead to characteristically different products depending on whether the diene is conjugated or non-conjugated.

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