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Amide (A)–thioamide (T) interconversions using Ph 3 SiSH (A to T) and Ph 3 SnOH (T to A) reagents
Author(s) -
AriasUgarte Renzo N,
Sharma Hemant K,
Pannell Keith H
Publication year - 2016
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3462
Subject(s) - thioamide , chemistry , amide , reagent , medicinal chemistry , tin , stereochemistry , organic chemistry
Ph 3 SiSH transforms amides to thioamides and Ph 3 SnOH performs the reverse process, with the concomitant formation of Ph 3 SiOH (or Ph 3 SiOSiPh 3 ) and Ph 3 SnSSnPh 3 , respectively. The chemistry is a delightful illustration of the oxophilicity of silicon compared to the thiophilicity of tin and occurs under relatively mild conditions, and for amide to thioamide transformation requires no amide activation. The chemistry is in accord with available data for Si(S)(O), Sn(O)(S) and C(O)(S) bond energies. Copyright © 2016 John Wiley & Sons, Ltd.