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Conversion of Amines into Phenylsulfides and Phenylselenides via Ditosylamides
Author(s) -
Müller Paul,
Thi Minh Phuong Nguyen
Publication year - 1980
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.19800630806
Subject(s) - chemistry , nucleophile , inversion (geology) , combinatorial chemistry , simple (philosophy) , displacement (psychology) , organic chemistry , stereochemistry , catalysis , psychology , paleontology , philosophy , epistemology , structural basin , psychotherapist , biology
Amines are converted in good to excellent yields to phenylsulfides or phenyl‐selenides via nucleophilic displacement on the corresponding ditosylamides. The conversion of (−)‐( S )‐1‐phenylethylamine to the chiral phenylsulfide 6 was found to proceed with inversion of configuration. A simple one‐pot procedure for the preparation of ditosylamides is reported.