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A Practical Synthesis of Thiopyrylium Tetrafluoroborate from Ethyl Vinyl Sulfide
Author(s) -
Poleschner Helmut,
Seppelt Konrad
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200107)2001:13<2477::aid-ejoc2477>3.0.co;2-h
Subject(s) - tetrafluoroborate , chemistry , propargyl , sulfide , yield (engineering) , single crystal , medicinal chemistry , organic chemistry , ionic liquid , catalysis , crystallography , materials science , metallurgy
A new, efficient synthesis of thiopyrylium tetrafluoroborate (C 5 H 5 S + BF 4 − ) is described. It is based on the three‐step sequence ethyl vinyl sulfide → propargyl vinyl sulfide → 2 H ‐thiopyran → C 5 H 5 S + BF 4 − in an overall yield of 54%. Preparations of C 5 H 5 S + BPh 4 − , C 5 H 5 S + I − , and C 5 H 5 S + CF 3 SO 3 − (TfO − ) are also described. The latter is the subject of the first X‐ray single crystal structure determination of the thiopyrylium ion.