|
| Section2 = | Section5 = }} Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. It is an ether. ==Reactivity== Anisole undergoes electrophilic aromatic substitution reaction more quickly than does benzene, which in turn reacts more quickly than nitrobenzene. The methoxy group is an ortho/para directing group, which means that electrophilic substitution preferentially occurs at these three sites. The enhanced nucleophilicity of anisole vs benzene reflects the influence of the methoxy group, which renders the ring more electron-rich. The methoxy group strongly affects the pi cloud of the ring as a mesomeric electron donor, more so than as an inductive electron withdrawing group despite the electronegativity of the oxygen. Illustrative of its nucleophilicity, anisole reacts with acetic anhydride to give 4-methoxyacetophenone: :CH3OC6H5 + (CH3CO)2O → CH3OC6H4C(O)CH3 + CH3CO2H Unlike most acetophenones, but reflecting the influence of the methoxy group, methoxyacetophenone undergoes a second acetylation. Many related reactions have been demonstrated. For example, P4S10 converts anisole to Lawesson's reagent, ()2. The ether linkage is highly stable, but the methyl group can be removed with hydroiodic acid: :CH3OC6H5 + HI → HOC6H5 + CH3I 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Anisole」の詳細全文を読む スポンサード リンク
|