51469-63-7Relevant academic research and scientific papers
Stevens rearrangement of thioethers with arynes: A facile access to multi-substituted β-keto thioethers
Xu, Xiao-Bo,Lin, Zi-Hua,Liu, Yuyin,Guo, Jian,He, Yun
supporting information, p. 2716 - 2720 (2017/04/03)
An effective method for the synthesis of multi-substituted β-keto thioethers via Stevens rearrangement of simple β-keto thioethers with arynes has been developed. In these reactions, successive C-S/C-H/C-C bonds were formed in one pot under mild and transition-metal free conditions to afford multi-substituted β-keto thioethers in moderate to good yields.
Mass Spectrometry of 2-Alkylthio-2-methylpropanoic Acids and Their Esters and Amides. Structural and Steric Effects on the McLafferty Rearrangement
Mori, Yuji,Fujiwara, Shigeru,Miyachi, Toshiko,Kitanishi, Hiroyuki,Oya, Masayuki,et al.
, p. 1505 - 1517 (2007/10/02)
The electron ionization mass spectra (MS) of S-methylated derivatives of N-(2-mercapto-2-methylpropanoyl)-L-cysteine and 2-alkylthio-2-methylpropanoic acids, as well as their esters and amides, were examined.Use of the deuterium labeling technique and accurate mass measurement supported the proposed fragmentation pathways.Extensive loss of CH2S from a molecular ion by the McLafferty rearrangementof a primary hydrogen is important in the MS of S-methyl compounds of amide derivatives.It was demonstrated that the intensity of the rearrangement ion decreases in the order of amide, ester, and acid, and in the case if amides the reaarangement is suppressed by the nonbonded interaction between methyl groups on the α carbon and the amide nitrogen.Keywords-N-(2-mercapto-2-methylpropanoyl)-L-cysteine; 2-alkylthio-2-methylpropanoic acid and methyl ester; 2-alkylthio-2-methylpropanamide; electron impact mass spectrometry; McLafferty rearrangement; steric interaction
