By M.F. Semmelhack
Quantity four specializes in additions and the ensuing substitutions at carbon-carbon &pgr;-bonds. half 1 contains strategies ordinarily regarded as basic polar reactions, reactive electrophiles and nucleophiles including to alkenes and alkynes. a big subject is Michael-type addition to electron poor &pgr;-bonds, featured within the first six chapters. partly 2 are amassed the 4 normal tactics resulting in nucleophilic fragrant substitution, together with radical chain tactics and transition steel activation via to &pgr;-complexation. Metal-activated addition (generally through nucleophiles) to alkenes and polyenes is gifted partially three, together with allylic alkylation catalyzed by means of palladium. The insurance of nonpolar additions partly four contains radical additions, organometal addition (Heck reaction), carbene addition, and 1,3-dipolar cycloadditions.
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Extra info for Additions to and Substitutions at C-C &pgr;-Bonds, Volume 4
The next day (total reaction time = 10 to 14 h), the reaction mixture is suspended in CH2Cl2 and washed sequentially with buffer (pH 4, Aldrich), satd. aq. NaCl, satd. aq. NaHCO3, and satd. aq. NaCl. Drying (Na2SO4) and concentration in vacuo affords the crude product, which is puriﬁed by silica gel ﬂash chromatography. 51) . This reagent has been prepared by mixing Ph3P=O and (FSO2)O and used in situ for esteriﬁcation. It is assumed that the reaction proceeds through an acyloxy- or alkoxyphosphonium intermediate.
1 Reaction with Carboxylic Acids intermediates are generated by reaction of triphenylphosphine with N-bromo or iodo succinimide, treatment of which with alcohol furnishes esters . 48  A mixture of benzoic acid (24 mmol), phenol (20 mmol), carbon tetrachloride (24 mmol), triethylamine (24 mmol), and triphenylphosphine (24 mmol) in acetonitrile (30 mL) is stirred at room temperature for 4 h. After the acetonitrile has been evaporated, hexane is added to the residue. The hexane solution is ﬁltered, removing the precipitated triphenylphosphine oxide and triethylamine hydrochloride, washed with an aqueous sodium hydroxide solution, and dried over anhydrous sodium sulfate, and then the hexane is removed.
After evaporation of the solvent in vacuo, the product is puriﬁed by silica gel column chromatography. 35 Iminophosphorane functions as an alternative to the alkoxyphosphonium salt . 36). Heating of a mixture of alcohol, carboxylic acid, benzyl azide, and triphenylphosphine thus affords the desired esters in good to excellent yields. ) in THF is heated to reﬂux and concentrated to give a crude product, which is puriﬁed by column chromatography. 37) [219, 220]. 4 moles of tertiary amine provides good to excellent yields of esters.
Additions to and Substitutions at C-C &pgr;-Bonds, Volume 4 by M.F. Semmelhack