Alkane synthesis

Takamizawa, K., Ogawa, Y. and Oyama, T. Thermal behavior of n-alkanes synthesized with attention paid to high purity. Polymer J. 14, 441 (1982)... 

Even in the largest cyclic alkane synthesized, c-(CH2)288, only the extended ring conformation has been observed, i.e., the two stems constituting the collapsed ring did not fold further.31... 

Catalytic hydrogenolysis of alkyl halides is one of the classical methods of alkane syntheses. Among other catalysts, Raney Ni has proved to be quite effective for the hydrogenolysis of iodides (equation 39) . A relatively recent discovery is the reductive dehalogenation of alkyl halides under the conditions of ionic hydrogenation. 

The emergence of radical addition to olefins as a powerful C—C bond forming reaction offers many possible applications in alkane syntheses In its intramolecular mode, the reaction is extremely well suited for carboxylic ring construction with regio- and stereochemical control. A vast array of polycycloalkane skeletons present in natural products... 

Chiral active pharmaceutical ingredients, 18 725-726. See also Enantio- entries Chiral additives, 6 75—79 Chiral alcohols, synthesis of, 13 667-668 P-Chiral alcohols, synthesis of, 13 669 Chiral alkanes, synthesis of, 13 668-669 Chiral alkenes, synthesis of, 13 668—669 Chiral alkoxides, 26 929 Chiral alkynes, synthesis of, 13 668-669 Chiral ammonium ions, enantiomer recognition properties for, 16 790 Chiral ansa-metallocenes, 16 90 Chiral auxiliaries, in oxazolidinone formation, 17 738—739... 

Side Note 1.5. An (Almost) Universal C,C Bond-Forming Alkane Synthesis... 

Tosylhydrazones can be silylated with (fert-bufyldimethylsilyl)trifluoromethanesulfonate (Me2teriBuSi03SCF3) on the sulfonamide nitrogen. This is how the starting material for a broadly applicable alkane synthesis is produced ( Figure 1.49). Due to their ability to undergo reductive cyanization (Figure 17.69) mesitylene sulfonyl hydrazones allow for a two-step synthesis of nitriles from ketones. 

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