Premium
Synthesis of t ‐butyl‐ 2 H 9 ‐thiophenes
Author(s) -
Fowler Rosemary G.,
Higgins Robert W.
Publication year - 1970
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590060412
Subject(s) - thiophene , bromide , chemistry , chloride , deuterium , medicinal chemistry , organic chemistry , physics , quantum mechanics
Interaction of 2‐thienylmagnesium bromide with t‐butyl chloride 2 H 9 yielded 2‐(t‐butyl‐ 2 H 9 ) thiophene and 3‐(t‐butyl 2 H 9 ) thiophene. Likewise, interaction of 5‐t‐butyl‐2‐thienylmagnesium bromide with t‐butyl chloride‐ 2 H 9 yielded 2,4‐di(t‐butyl‐4‐ 2 H 9 ) thiophene and 2,5‐di(t‐butyl‐5‐ 2 H 9 ) thiophene. The labeled mono‐t‐butyl‐thiophenes and the labeled di‐t‐butylthiophenes were separated by preparative gas chromatography. The structures of the four labeled compounds were established from infrared and nuclear magnetic resonance spectra. Nuclear magnetic resonance and mass spectral data indicated that each of the deuterium labeled isomers were of high isotopic purity (99.22 % or better).