Universal alkane synthesis

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

A highly versatile method for the synthesis of alkanes and other hydrocarbons from organic halides has been developed by E. J. Corey (Harvard University, Nobel Prize for Chemistry in 1990), G. H. Posner (The Johns Hopkins University), and by G. M. Whitesides (Harvard University) and H. O. House (Georgia Institute of Technology). 

This volume consists of reviews devoted to a range of important subjects. Vadim Guliants and Moises Carreon (University of Cincinnati) review the selective oxidation of butane. This is an excellent example of a catalytic process designed to add value to an inexpensive raw material, and is the only vapor phase selective oxidation of an alkane that is practiced industrially. This process also avoids the use of benzene, which eliminates the risk of handling this carcinogenic compound. The authors review the synthesis, activation, and mechanism of this reaction on V-P-O catalysts. 

A method of almost universal applicability for the deoxygenation of carbonyl compounds is the Wolff-Kishner reduction While the earlier reductions were carried out in two steps on the derived hydrazone or semicarbazone derivatives, the Huang-Minlon modification is a single-pot operation. In this procedure, the carbonyl compound and hydrazine (hydrate or anhydrous) are heated (180-220 °C) in the presence of a base and a proton source. Sodium or potassium hydroxide, potassium-t-butoxide and other alkoxides are the frequently used bases and ethylene glycol or its oligomers are used as the solvent and proton source. Over the years, several modifications of this procedure have been used to cater to the specific needs of a given substrate. The Wolff-Kishner reaction works well with both aldehydes and ketones and remains the most routinely used procedure for the preparation of alkanes from carbonyl compounds (Table 9). This method is equally suitable for the synthesis of polycyclic and hindered alkanes. 

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