1431213-85-2Relevant academic research and scientific papers
Nucleophile-dependent regioselective reaction of (S)-4-benzyl-2- fluoroalkyl-1,3-oxazolines
Jiang, Haizhen,Yan, Liuming,Xu, Minjun,Lu, Wenjun,Cai, Yeshan,Wan, Wen,Yao, Jianhua,Wu, Shaoxiong,Zhu, Shizheng,Hao, Jian
, p. 4261 - 4269 (2013/06/26)
Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (SRN1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the C=N bond.
