Comprehensive Organic Functional Group Transformations: Synthesis: carbon with one heteroatom attached by a single bond

acetic acid addition alcohols aldehydes alkanethiols alkenes alkenyl alkyl halides alkylarsines alkyllithium alkynes allylic anion antimony aromatic aryl arylphosphonous asymmetric benzylic bond borane boron bromides carbon carbonyl compounds catalyst chiral chloride cleavage CO₂Et CO₂H CO₂Me complexes converted corresponding cyclic derivatives dialkyl dichloride disulfides electrophilic enamines enantiomeric enantiomeric excess enol epoxides esters Et2O Et3N ethers example fluoride formation give Grignard reagents H₂O halogen high yields hydrazine hydride hydroboration hydrogen hydrolysis hydroxylamines intermediate iodides iodine ketones ligands lithium metal method mixture nucleophilic obtained organometallic oxidation peroxide Ph Ph phenols phosphine oxides phosphorus potassium prepared presence primary amines R¹ R2 react reaction reactive rearrangement reduction reflux regioselectivity RI R2 salts secondary amines selenides shown in Equation silyl sodium solvent stereoselective substituted substrates sulfide sulfinic acids sulfones sulfonyl sulfonyl chlorides sulfoxides sulfur synthesis synthetic temperature tertiary phosphines thiols transmetallation treatment undergo vinyl yields Equation