142653-59-6Relevant articles and documents
Pentafluorosulfanylbenzene chemistry: Role of copper in the Sheppard reaction, direct fluorination of aromatic sulfenyl chlorides, and several potentially energetic SF5-benzenes Dedicated to Teruo Umemoto in recognition of his being awarded the
Sipyagin, Alexey M.,Bateman, Colin P.,Matsev, Andrej V.,Waterfeld, Alfred,Jilek, Robert E.,Key, Christopher D.,Szulczewski, Gregory J.,Thrasher, Joseph S.
, p. 203 - 210 (2014)
In honor of the awardee Dr. Teruo Umemoto and his significant advances in the preparation of pentafluorosulfanylbenzenes [1], we will first overview our results aimed at understanding the importance of copper (and other coinage metals) in W.A. Sheppard's
Mono- and dinitration of pentafluorosulfanylbenzenes with [NO 2][BF4], and substrate selectivity (PhSF5 vs PhCF3 and PhSF5 vs PhNO2) in competitive nitration
Okazaki, Takao,Laali, Kenneth K.
, p. 96 - 100 (2014/08/05)
PhSF5 1 reacts with NO2+BF 4-/TfOH in CH2Cl2 (DCM) at room temperature to give 1-nitro-3-(pentafluorosulfanyl)benzene 2 in near quantitative yield. The dinitro derivative 4 is synthesized from 2 by reaction with NO2+BF4-/TfOH at 70 °C. The p-MeC6H4SF5 is mononitrated at room temperature with NO2+BF4-/DCM and dinitrated with NO2+BF4-/TfOH. Substrate selectivity (kPhSF5kRPh) in competitive nitration for PhSF5/PhCF3 and PhSF5/PhNO 2 with NO2+BF4- in DCM at room temperature was determined at 21.3 and ～1 respectively. Relative stability of the corresponding benzenium ions were gauged by DFT from the isodesmic proton transfer reaction SF5-C6H 6+ + R-C6H5 → SF 5-C6H5 + R-C6H6 + (R = CF3 and NO2). These studies indicate that reactivity of ArSF5 in SEAr is similar to ArNO 2.
