71119-01-2Relevant academic research and scientific papers
Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates
Matsuo, Yutaka,Yu, Yun,Yang, Xiao-Yu,Ueno, Hiroshi,Okada, Hiroshi,Shibuya, Hiromasa,Choi, Yeong Suk,Jin, Yong Wan
supporting information, p. 6270 - 6277 (2019/05/24)
Benzothieno[60]fullerenes were synthesized using fullerenyl cations as key intermediates. The reaction proceeded through a nucleophilic attack of the sulfur atom as a weak nucleophile to the fullerenyl cation electrophile. A monoarylated fullerene, (2-methylthiophenyl)hydro[60]fullerene, C60ArH (Ar = C6H4-SMe-2 and so on; four derivatives) was subjected to deprotonation with KOtBu to form a fullerenyl anion ArC60-, followed by oxidation using I2 to generate a fullerenyl cation ArC60+, leading to intramolecular demethylative cyclization via fullerene cation-S interaction to the product. Electrochemical and computational studies revealed slightly narrower band gap of this compound than usual fullerene derivatives because of the relatively high-lying HOMO of the fused thieno moiety.
Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates
Matsuo, Yutaka,Yu, Yun,Yang, Xiao-Yu,Ueno, Hiroshi,Okada, Hiroshi,Shibuya, Hiromasa,Choi, Yeong Suk,Jin, Yong Wan
, (2019/05/22)
Benzothieno[60]fullerenes were synthesized using fullerenyl cations as key intermediates. The reaction proceeded through a nucleophilic attack of the sulfur atom as a weak nucleophile to the fullerenyl cation electrophile. A monoarylated fullerene, (2-methylthiophenyl)hydro[60]fullerene, C60ArH (Ar = C6H4-SMe-2 and so on; four derivatives) was subjected to deprotonation with KOtBu to form a fullerenyl anion ArC60-, followed by oxidation using I2 to generate a fullerenyl cation ArC60+, leading to intramolecular demethylative cyclization via fullerene cation-S interaction to the product. Electrochemical and computational studies revealed slightly narrower band gap of this compound than usual fullerene derivatives because of the relatively high-lying HOMO of the fused thieno moiety.
A highly efficient approach to vanillin starting from 4-cresol
Jiang, Jian-An,Chen, Cheng,Guo, Ying,Liao, Dao-Hua,Pan, Xian-Dao,Ji, Ya-Fei
supporting information, p. 2807 - 2814 (2014/05/06)
A highly efficient approach to the famous flavor and fragrance compound vanillin has been developed starting from 4-cresol with the attention focused on improving the sustainability of all the reactions. The approach involves a three-step sequence of the quasi-quantitative selective clean oxybromination of 4-cresol, the high-yield selective aerobic oxidation of 2-bromo-4-cresol, and the quantitative methoxylation of 3-bromo-4-hydroxybenzaldehyde with the recovery of pure methanol. Herein, the pivotal oxidation and methoxylation reactions are logically investigated and developed into two concise methodologies. As a green alternative, the approach holds significant value for the sustainable manufacturing of vanillin. the Partner Organisations 2014.
