徳島大学 教育・研究者情報データベース(EDB)

1. 徳島大学.総合科学部.総合理数学科.物質総合コース(2009年4月1日〜)

1. 三好 德和([徳島大学.大学院社会産業理工学研究部.理工学域.自然科学系.化学分野]/[徳島大学.理工学部.理工学科.自然科学コース.化学講座])

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2. 菊池 淳

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3. 和田 眞

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(英) The Development of the New Synthetic Methods Using Metallic Strontium

(日) 金属ストロンチウムを用いる新しい合成手法の開発

(英) We found the interesting results that alkylation of carboxylic acids with methyl iodide using strontium metal proceeded smoothly to afford the corresponding monomethylated ketones, rather than the dimethylated alcohols, preferentially in moderate to good yields. Using the carboxylic acid sodium salt, the yield decreases slightly, but the reaction controls the over-addition of methyla-ting agent to give the dramatically improvement with high selectivities. Next, when benzoic acid reacted with metallic strontium and alkyl iodides, the unexpected reactions occurred to give <I>p</I>-alkylated products of the aromatic ring of benzoic acid in a trace amount. We were interested in the <I>p</I>-allylated product because this allylation reaction is unusual in these conditions and there are only a few reports of the <I>p</I>-alkylation of aromatic carbonyl compounds. As the results of various investigations, the <I>p</I>-alkylated products were obtained predominantly in good yields. Furthermore, it was found that the convenient bulky <I>tert</I>-benzylic alcohol benzoates were prepared by the dialkylation of methyl benzoate with methyl or <I>i</I>-butyl iodide in the presence of metallic strontium, followed by the addition of benzoyl chloride, benzoic anhydride or acetic anhydride as two portions.

1. 有機化学(organic chemistry)