Xiaoling Huang, B. J. Blackburn, S. Au-Yeung
Mar 1, 1990
Citations
0
Influential Citations
9
Citations
Journal
Canadian Journal of Chemistry
Abstract
The reaction of XeF2 with cysteine derivatives RSCH2CH(NHR)COOR, i.e., S-benzyl-N-trifluoroacetyl-L-cysteine methyl ester, S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester, and S-methyl-N-trifluoroacetyl-L-cysteine methyl ester is described. The fluorinated products PhCHFSCH2CH(NHR)COOR, PhCH2SCHFCH(NHR)COOR, and FCH2SCH2CH(NHR)COOR were identified by 1H and 19F nuclear magnetic resonance spectroscopy. PhCH2SCHFCH(NHR)COOR loses HF within 24 hours to give Z- and E-PhCH2SCH=C(NHR)COOR. If the reaction with XeF2 is carried out in the presence of moisture the sulfoxide RS(O)CH2CH(NHR)COOR and sulfone RSO2CH2CH(NHR)COOR are produced. Keywords: fluorination, XeF2, amino acids, cysteine.