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Under the optimized conditions (method A),11 a variety of organothiols were oxidized smoothly to produce disulfides 1a–r in good to excellent yields (Table 1). Diphenyl disulfide 1a was obtained in 98% isolated yield after 3 h at 60 C (Table 1, entry 1). Diaryl disulfides containing electron donating (Table 1, entries 2–4) and electron withdrawing groups (Table 1, entries 5–8), could be obtained in high yields. Good yields of oxidation were obtained using 2-amino-4-chlorobenzenethiol and 2-naphthalenethiol (Table 1, entries 9 and 10). Excellent yield of the disulfide was obtained with 2-mercaptobenzothiazole but this reaction was performed at 100 C (Table 1, entry 11). Satisfactory results were achieved using benzylic or alkylic thiols yielding the corresponding disufides 1l–q in a range of 80–99% (Table 1, entries 12–17). Additionally, the amino acid L-cysteine, which is involved in a large number of biological processes, is converted into cystine 1r with 87% yield (Table 1, entry 18). In order to obtain an efficient protocol in terms of energy economy, we performed these reactions under microwave irradiation. Thus, the mixture of benzenethiol (1.0 mmol) and [bmim][- SeO2(OCH3)] was irradiated under stirring and fortunately, after 15 min at 30 C, diphenyl disulfide 1a was obtained in 98% (method B).11 To extend the scope of method B, other organothiols were irradiated with microwaves and the corresponding disulfides shown in Table 2 were obtained in excellent yields. Finally, a study regarding the recovering and reusing of the ionic liquid was also performed using the method B. After the total oxidation of benzenethiol, the product was extracted with petroleum ether (3 5 mL). The upper phase was dried and the solvent evaporated. |
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至尊木虫 (职业作家)
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2楼2012-05-04 11:05:15
3楼2012-05-04 11:14:03
频回眄睐
至尊木虫 (职业作家)
- 翻译EPI: 110
- 应助: 13 (小学生)
- 贵宾: 0.566
- 金币: 17176.4
- 散金: 1586
- 红花: 30
- 沙发: 3
- 帖子: 3337
- 在线: 545.1小时
- 虫号: 1238300
- 注册: 2011-03-19
- 性别: GG
- 专业: 金属有机化学
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转弯为你相遇: 金币+50, 翻译EPI+1, ★★★很有帮助, 谢谢你的帮助 2012-05-04 12:25:46
转弯为你相遇: 金币+50, 翻译EPI+1, ★★★很有帮助, 谢谢你的帮助 2012-05-04 12:25:46
| 对于苄型和烷基型硫代化合物进行二硫化我们也得到了满意的结果，产率在 80–99% 之间(表1, 12–17)。另外，具有重要生物活性的L－半光氨酸能以87%的产率转化成胱氨酸 (表 1, 18).为了从能源节约角度上获得一种有效的方法，我们在微波下尝试了该反应。将苯硫酚 (1.0 mmol) 和 [bmim][－SeO2(OCH3)] 的混合物在30度下微波搅拌15min，我们幸运地得到了二苯基二硫代化合物1a ，产率为98% (methodB).11。为了扩大方法B的应用范围， 我们将一系列有机硫代化合物在微波照射下反应，得到了相应的优秀产率的二硫代化合物如表2所示。最后我们用无机溶液来重复方法B。在苯硫酚完全氧化后，用石油醚(3 5 mL).萃取，上层有机相干燥，真空除去溶剂即得产物。 |
4楼2012-05-04 11:55:03