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A Novel Synthesis of tert ‐ Alkyl Sulfides
Author(s) -
Katritzky Alan R.,
Perumal Subbu,
Kuzmierkiewicz Wojciech,
Lue Ping,
Greenhill John V.
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740829
Subject(s) - chemistry , alkyl , benzotriazole , halogen , electrophile , halide , reagent , medicinal chemistry , sulfonium , organic chemistry , catalysis , salt (chemistry)
tert ‐ Alkyl sulfides are conveniently prepared from α‐(1 H ‐benzotriazol‐1‐yl)alkyl sulfides by displacement of the 1 H ‐benzotriazol‐1‐yl group with Grignard reagents. The 1‐[α‐(alkylthio)alkyl]‐ and 1‐[α‐(arylthio)alkyl]‐1 H ‐benzotriazole intermediates are easily available by several routes: ( i ) displacement of the halogen from appropriate halides by sodium salts of thiols, ( ii ) condensation of 1 H ‐benzotriazole and thiols with carbonyl compounds, or ( iii ) lithiation of N ‐substituted 1 H ‐benzotriazoles and subsequent treatment with electrophiles.