29922-56-3Relevant articles and documents
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 Quantitative Assay of Sodium Triacetoxyborohydride
Zacuto, Michael J.,Perona, Joseph,Dunn, Robert
, p. 2080 - 2087 (2019/09/09)
Sodium triacetoxyborohydride (STAB) is a common reducing agent with potency that degrades over time and is not uniformly assigned. A simple assay based on an aldehyde reduction has been developed to determine the active borohydride content of this reagent. The HPLC assay yield of a salicylaldehyde reduction has been shown to accurately determine this potency and has been validated against the H2 evolution method as well as yields obtained from a reductive amination. The use of these assay data to adjust the STAB charge as well to optimize a reductive amination has been demonstrated.
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.